Substituted phthalimidocinnamic acid derivatives and intermediates for their preparation

ABSTRACT

Substituted phthalimidocinnamic acid derivatives I ##STR1## wherein the variables are as defined in the description are useful as herbicides and for the desication and/or defoliation of plants.

This application is a 371 of PCT/EP95/04067 filed Oct. 17, 1995.

The present invention relates to novel substituted phthalimidocinnamicacid derivatives of the formula I ##STR2## where R¹ is hydrogen or C₁-C₄ -alkyl;

R² is hydrogen or halogen;

R³ is cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆-alkoxy or C₁ -C₆ -haloalkoxy;

R⁴ is hydrogen, cyano, nitro, halogen or C₁ -C₆ -alkyl;

R⁵ is hydrogen, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₁ -C₆-haloalkyl, C₁ -C₆ -cyanoalkyl, C₁ -C₆ -hydroxyalkyl, C₁ -C₆-mercaptoalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl or C₁ -C₆ -alkylthio-C₁ -C₆-alkyl;

R⁶ is one of the radicals stated under R⁵ or cyano, nitro, C₁ -C₆-alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -haloalkylthio,C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl, hydroxycarbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkylamino)carbonyl-C₁ -C₆ -alkyl, di(C₁ -C₆ -alkyl)aminocarbonyl-C₁-C₆ -alkyl, aminocarbonyl-C₁ -C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl-C₁ -C₆-alkyl, C₁ -C₆ -alkoximino-C₁ -C₆ -alkyl, hydroximino-C₁ -C₆ -alkyl,di(C₁ -C₆ -alkoxy)-C₁ -C₆ -alkyl, di(C₁ -C₆ -alkylthio)-C₁ -C₆ -alkyl,C₃ -C₆ -haloalkenyl, (C₁ -C₆ -alkoxy)carbonyl, hydroxycarbonyl, (C₁ -C₆-alkylamino)carbonyl, di(C₁ -C₆ -alkyl)aminocarbonyl, aminocarbonyl(C₁-C₆ -alkyl)carbonyl, (C₁ -C₆ -haloalkyl)carbonyl, aryl, hetaryl, aryl-C₁-C₆ -alkyl or hetaryl-C₁ -C₆ -alkyl, where the aryl and hetaryl ringsmay, if desired, carry from one to three radicals selected from thegroup consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio, C₁-C₆ -haloalkylthio, hydroxyl, mercapto and (C₁ -C₆ -alkoxy)carbonyl;

or

R⁵ and R⁶ together form a two-membered to six-membered alkylene chain inwhich a methylene unit may be replaced by oxygen or C₁ -C₄ -alkylimino;

R⁷ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₂ -C₆-haloalkyl, C₁ -C₆ -cyanoalkyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₁ -C₆-alkylthio-C₂ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, C₃ -C₆-cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₆ -alkyl,

phenyl or benzyl, where the phenyl rings may each carry from one tothree radicals selected from the group consisting of cyano, nitro,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆-haloalkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -haloalkylthio and (C₁ -C₆-alkoxy)carbonyl;

X is oxygen, sulfur or --N(R⁸)--, and

R⁸ is one of the radicals stated under R⁷ or is (C₁ -C₆-alkoxy)carbonyl, (C₁ -C₆ -haloalkoxy)carbonyl, (C₁ -C₆ -alkyl)carbonyl,(C₁ -C₆ -haloalkyl)carbonyl, tri(C₁ -C₆ -alkyl)silyl, aryloxycarbonyl orarylmethoxycarbonyl

or, together with R⁶, is a three-membered to 5-membered alkylene chainin which a nonterminal methylene unit may be replaced by oxygen or C₁-C₄ -alkylimino or in which the N-bonded methylene unit may be replacedby carbonyl,

and the agriculturally useful salts of I.

The present invention furthermore relates to novel intermediates of theformulae IIa and IIb, where R² to R⁷ and X have the same meanings as inthe case of the compounds I.

The present invention furthermore relates to

the use of the compounds I as herbicides and/or for the desiccationand/or defoliation of plants,

herbicides and plant desiccants and/or defoliants which contain thecompounds I as active ingredients,

processes for the preparation of the compounds I and of herbicides andplant desiccants and/or defoliants using the compounds I and

methods for controlling undesirable plant growth and for desiccatingand/or defoliating plants with the compounds I.

EP-A 240 659, EP-A 300 387 and EP-A 400 427 disclose herbicidal cinnamicacid derivatives. However, their action is not always completelysatisfactory, especially at low application rates.

It is an object of the present invention to provide cinnamic acidderivatives having improved herbicidal activity.

We have found that this object is achieved by the substitutedphthalimidocinnamic acid derivatives of the formula I which are definedat the outset. We have also found herbicides which contain the compoundsI and have very good herbicidal activity. We have furthermore foundprocesses for the preparation of these agents and methods forcontrolling undesirable plant growth with the compounds I.

The novel compounds I are furthermore suitable for defoliating anddesiccating plant parts for, for example, cotton, potato, rape,sunflower, soybeans or field beans, in particular for cotton. Plantdesiccants and/or defoliants, processes for the preparation of theseagents and methods for desiccating and/or defoliating plants with thecompounds I were found for this purpose.

Depending on the substitution pattern, the compounds of the formula Imay contain one or more centers of chirality and are then present asenantiomer or diastereomer mixtures. The present invention relates bothto the pure enantiomers or diastereomers and to mixtures thereof.

The substituted phthalimidocinnamic acid derivatives I may be present inthe form of their agriculturally useful salts, the type of saltgenerally being unimportant. In general, the salts of those bases andthose acid addition salts in which the herbicidal activity is notadversely affected compared with the free compound I are suitable.

Particularly suitable basic salts are those of the alkali metals,preferably sodium and potassium salts, of the alkaline earth metals,preferably calcium and magnesium salts, those of the transition metals,preferably zinc and iron salts, and ammonium salts in which the ammoniumion can, if desired, carry from one to three C₁ -C₄ -alkyl or hydroxy-C₁-C₄ -alkyl substituents and/or one phenyl or benzyl substituent,preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium,trimethylbenzylammonium and trimethyl(2-hydroxyethyl)ammonium salts, aswell as phosphonium salts, sulfonium salts, preferably tri(C₁ -C₄-alkyl)sulfonium salts, and sulfoxonium salts, preferably tri(C₁ -C₄-alkyl)sulfoxonium salts.

Among the acid addition salts, the hydrochlorides, hydrobromides,sulfates, nitrates, phosphates, oxalates and dodecylbenzenesulfonatesmay be mentioned in the first place.

The organic moieties stated for R¹ to R⁸ or as radicals on phenyl, arylor hetaryl rings are, like the term halogen, general terms forindividual lists of the specific group members. All carbon chains, ie.all alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, haloalkoxy,haloalkylthio, alkenyloxy, alkynyloxy, alkoxycarbonyl, alkylimino oralkoximino moieties, may be straight-chain or branched. Halogenatedsubstituents preferably carry from one to five identical or differenthalogen atoms.

Specific examples are as follows:

halogen is fluorine, chlorine, bromine or iodine;

C₁ -C₄ -alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;

C₁ -C₆ -alkyl and the alkyl moieties of C₃ -C₆ -cycloalkyl-C₁ -C₆-alkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, di(C₁ -C₆ -alkoxy)-C₁ -C₆ -alkyl,C₁ -C₆ -alkylthio-C₁ -C₆ -alkyl, di(C₁ -C₆ -alkylthio)-C₁ C₆ -alkyl, (C₁-C₆ -alkyl)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆-alkyl, C₁ -C₆ -alkoximino-C₁ -C₆ -alkyl, (C₁ -C₆-alkylamino)carbonyl-C₁ -C₆ -alkyl, di(C₁ -C₆ -alkyl)aminocarbonyl-C₁-C₆ -alkyl, tri(C₁ -C₆ -alkyl)silyl, aryl-C₁ -C₆ -alkyl and hetaryl-C₁-C₆ -alkyl are each one of the radicals stated for C₁ -C₄ -alkyl or areeach n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, 1,1-di-methylpropyl,1,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-di-methylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-di-methylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl;

the alkyl moieties of C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl and C₁ -C₆-alkylthio-C₂ -C₆ -alkyl are each ethyl, n-propyl, 1-methylethyl,n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl or one of theradicals additionally stated for C₁ -C₆ -alkyl;

C₂ -C₆ -haloalkyl is C₁ -C₆ -alkyl as stated above, with the exceptionof methyl which is partially or completely substituted by fluorine,chlorine, bromine and/or iodine, eg. 2-fluoroethyl, 2-chloroethyl,2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl,2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl,4-bromobutyl, nonafluorobutyl, 5-fluoropentyl, 5-chloropentyl,5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl,6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;

C₁ -C₆ -haloalkyl is C₁ -C₆ -alkyl as stated above which is partially orcompletely substituted by fluorine, chlorine, bromine and/or iodine, eg.chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl or one of the radicals statedfor C₂ -C₆ -haloalkyl;

C₃ -C₆ -cycloalkyl and the cycloalkyl moiety of C₃ -C₆ -cycloalkyl-C₁-C₆ -alkyl are each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

C₃ -C₆ -alkenyl is prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl,n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-en-1-yl,2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl or2-methylprop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl,n-penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl,3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl,3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl,1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl,n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl,

1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl,4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl,2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl,4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl,1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl,1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl,1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl,2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl,2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl,3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl,1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl,2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl,1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl or1-ethyl-2-methylprop-2-en-1-yl;

C₂ -C₆ -alkenyl is ethenyl or one of the radicals stated for C₃ -C₆-alkenyl;

C₃ -C₆ -haloalkenyl is C₃ -C₆ -alkenyl as stated above which ispartially or completely substituted by fluorine, chlorine and/orbromine, eg. 2-chloroallyl, 3-chloroallyl or 3,3-dichloroallyl;

C₃ -C₆ -alkynyl is prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn-1-yl,but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, n-pent-1-yn-1-yl,n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl,n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methyl-but-1-yn-3-yl,3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl,n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl,n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl,n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl,3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl,4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;

C₂ -C₆ -alkynyl is ethynyl or one of the radicals stated for C₃ -C₆-alkynyl;

C₁ -C₆ -cyanoalkyl is cyanomethyl, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl,1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanopropy-1-yl, 1-cyanoprop-2-yl,2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl,4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 1-cyanobut-3-yl,2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl, 2-cyano-2-methylprop-3-yl,3-cyano-2-methylprop-3-yl, 2-cyano-methylprop-2-yl, 1-cyanopent-1-yl,2-cyanopent-1-yl, 3-cyanopent-1-yl, 4-cyanopent-1-yl, 5-cyanopent-1-yl,1-cyanopent-2-yl, 2-cyanopent-2-yl, 1-cyanopent-3-yl, 2-cyanopent-3-yl,1-cyanopent-4-yl, 2-cyanopent-4-yl, 3-cyanopent-4-yl,1-cyano-2-ethylprop-3-yl, 1-cyanohex-1-yl, 2-cyanohex-1-yl,3-cyanohex-1-yl, 4-cyanohex-1-yl, 5-cyanohex-1-yl, 6-cyanohex-1-yl,1-cyanohex-2-yl, 2-cyanohex-2-yl, 1-cyanohex-3-yl, 2-cyanohex-3-yl,1-cyanohex-4-yl, 2-cyanohex-4-yl, 3-cyanohex-4-yl,1-cyano-2-ethylbut-3-yl, 1-cyano-2-ethylbut-4-yl or1-cyano-2-propylprop-3-yl;

C₁ -C₆ -hydroxyalkyl is hydroxymethyl, 1-hydroxyeth-1-yl,2-hydroxyeth-1-yl, 1-hydroxyprop-1-yl, 2-hydroxyprop-1-yl,3-hydroxyprop-1-yl, 1-hydroxyprop-2-yl, 2-hydroxyprop-2-yl,1-hydroxybut-1-yl, 2-hydroxybut-1-yl, 3-hydroxybut-1-yl,4-hydroxybut-1-yl, 1-hydroxybut-2-yl, 2-hydroxy-but-2-yl,1-hydroxybut-3-yl, 2-hydroxybut-3-yl, 1-hydroxy-2-methylprop-3-yl,2-hydroxy-2-methyl-prop-3-yl, 3-hydroxy-2-methylprop-3-yl,2-hydroxymethylprop-2-yl, 1-hydroxypent-1-yl, 2-hydroxypent-1-yl,3-hydroxypent-1-yl, 4-hydroxypent-1-yl, 5-hydroxypent-1-yl,1-hydroxypent-2-yl, 2-hydroxypent-2-yl, 1-hydroxypent-3-yl,2-hydroxypent-3-yl, 1-hydroxypent-4-yl, 2-hydroxypent-4-yl,3-hydroxypent-4-yl, 1-hydroxy-2-ethylprop-3-yl, 1-hydroxyhex-1-yl,2-hydroxyhex-1-yl, 3-hydroxyhex-1-yl, 4-hydroxyhex-1-yl,5-hydroxyhex-1-yl, 6-hydroxyhex-1-yl, 1-hydroxyhex-2-yl,2-hydroxyhex-2-yl, 1-hydroxyhex-3-yl, 2-hydroxyhex-3-yl,1-hydroxyhex-4-yl, 2-hydroxyhex-4-yl, 3-hydroxyhex-4-yl,1-hydroxy-2-ethylbut-3-yl, 1-hydroxy-2-ethylbut-4-yl or1-hydroxy-2-propylprop-3-yl;

C₁ -C₆ -mercaptoalkyl is mercaptomethyl, 1-mercaptoeth-1-yl,2-mercaptoeth-1-yl, 1-mercaptoprop-1-yl, 2-mercaptoprop-1-yl,3-mercaptoprop-1-yl, 1-mercaptoprop-2-yl, 2-mercaptoprop-2yl,1-mercaptobut-1-yl, 2-mercaptobut-1-yl, 3-mercaptobut-1-yl,4-mercaptobut-1-yl, 1-mercaptobut-2-yl, 2-mercapto-but-2-yl,1-mercaptobut-3-yl, 2-mercaptobut-3-yl, 1-mercapto-2-methylprop-3-yl,2-mercapto-2-methylprop-3-yl, 3-mercapto-2-methyl-prop-3-yl,2-mercaptomethylprop-2-yl, 1-mercaptopent-1-yl, 2-mercaptopent-1-yl,3-mercaptopent-1-yl, 4-mercaptopent-1-yl, 5-mercaptopent-1-yl,1-mercaptopent-2-yl, 2-mercaptopent-2-yl, 1-mercaptopent-3-yl,2-mercaptopent-3-yl, 1-mercaptopent-4-yl, 2-mercaptopent-4-yl,3-mercaptopent-4-yl, 1-mercapto-2-ethyl-prop-3-yl, 1-mercaptohex-1-yl,2-mercaptohex-1-yl, 3-mercaptohex-1-yl, 4-mercaptohex-1-yl,5-mercaptohex-1-yl, 6-mercaptohex-1-yl, 1-mercaptohex-2-yl,2-mercaptohex-2-yl, 1-mercaptohex-3-yl, 2-mercaptohex-3-yl,1-mercaptohex-4-yl, 2-mercaptohex-4-yl, 3-mercaptohex-4-yl,1-mercapto-2-ethylbut-3-yl, 1-mercapto-2-ethylbut-4-yl or1-mercapto-2-propylprop-3-yl;

hydroxycarbonyl-C₁ -C₆ -alkyl is hydroxycarbonylmethyl,1-(hydroxycarbonyl)eth-1-yl, 2-(hydroxycarbonyl)eth-1-yl,1-(hydroxycarbonyl)prop-1-yl, 2-(hydroxycarbonyl)prop-1-yl,3-(hydroxycarbonyl)prop-1-yl, 1-(hydroxycarbonyl)prop-2-yl,2-(hydroxycarbonyl)prop-2-yl, 1-(hydroxycarbonyl)but-1-yl,2-(hydroxycarbonyl)but-1-yl, 3-(hydroxycarbonyl)but-1-yl,4-(hydroxycarbonyl)but-1-yl, 1-(hydroxycarbonyl)but-2-yl,2-(hydroxycarbonyl)but-2-yl, 1-(hydroxycarbonyl)but-3-yl,2-(hydroxycarbonyl)but-3-yl, 1-(hydroxycarbonyl)-2-methylprop-3-yl,2-(hydroxycarbonyl)-2-methylprop-3-yl,3-(hydroxycarbonyl)-2-methylprop-3-yl,2-(hydroxycarbonylmethyl)prop-2-yl, 1-(hydroxycarbonyl)pent-1-yl,2-(hydroxycarbonyl)pent-1-yl, 3-(hydroxycarbonyl)pent-1-yl,4-(hydroxycarbonyl)pent-1-yl, 5-(hydroxycarbonyl)pent-1-yl,1-(hydroxycarbonyl)pent-2-yl, 2-(hydroxycarbonyl)pent-2-yl,1-(hydroxycarbonyl)pent-3-yl, 2-(hydroxycarbonyl)pent-3-yl,1-(hydroxycarbonyl)pent-4-yl, 2-(hydroxycarbonyl)pent-4-yl,3-(hydroxycarbonyl)pent-4-yl, 1-(hydroxycarbonyl)-2-ethylprop-3-yl,1-(hydroxycarbonyl)hex-1-yl, 2-(hydroxycarbonyl)hex-1-yl,3-(hydroxycarbonyl)hex-1-yl, 4-(hydroxycarbonyl)hex-1-yl,5-(hydroxycarbonyl)hex-1-yl, 6-(hydroxycarbonyl)hex-1-yl,1-(hydroxycarbonyl)hex-2-yl, 2-(hydroxycarbonyl)hex-2-yl,1-(hydroxycarbonyl)hex-3-yl, 2-(hydroxycarbonyl)hex-3-yl,1-(hydroxycarbonyl)hex-4-yl, 2-(hydroxycarbonyl)hex-4-yl,3-(hydroxycarbonyl)hex-4-yl, 1-(hydroxycarbonyl)-2-ethylbut-3-yl,1-(hydroxycarbonyl)-2-ethylbut-4-yl or1-(hydroxycarbonyl)-2-propylprop-3-yl;

hydroximino-C₁ -C₆ -alkyl is hydroximinomethyl, 1-(hydroximino)eth-1-yl,2-(hydroximino)eth-1-yl, 1-(hydroximino)prop-1-yl,2-(hydroximino)prop-1-yl, 3-(hydroximino)prop-1-yl,1-(hydroximino)prop-2-yl, 2-(hydroximino)prop-2-yl,1-(hydroximino)but-1-yl, 2-(hydroximino)but-1-yl,3-(hydroximino)but-1-yl, 4-(hydroximino)but-1-yl,1-(hydroximino)but-2-yl, 2-(hydroximino)but-2-yl,1-(hydroximino)but-3-yl, 2-(hydroximino)but-3-yl,1-(hydroximino)-2-methylprop-3-yl, 2-(hydroximino)-2-methylprop-3-yl,3-(hydroximino)-2-methylprop-3-yl, 2-(hydroximinomethyl)-prop-2-yl,1-(hydroximino)pent-1-yl, 2-(hydroximino)pent-1-yl,3-(hydroximino)pent-1-yl, 4-(hydroximino)pent-1-yl,5-(hydroximino)pent-1-yl, 1-(hydroximino)pent-2-yl,2-(hydroximino)pent-2-yl, 1-(hydroximino)pent-3-yl,2-(hydroximino)pent-3-yl, 1-(hydroximino)pent-4-yl,2-(hydroximino)pent-4-yl, 3-(hydroximino)pent-4-yl,1-(hydroximino)-2-ethylprop-3-yl, 1-(hydroximino)hex-1-yl,2-(hydroximino)hex-1-yl, 3-(hydroximino)hex-1-yl,4-(hydroximino)hex-1-yl, 5-(hydroximino)hex-1-yl,6-(hydroximino)hex-1-yl, 1-(hydroximino)hex-2-yl,2-(hydroximino)hex-2-yl, 1-(hydroximino)hex-3-yl,2-(hydroximino)hex-3-yl, 1-(hydroximino)hex-4-yl,2-(hydroximino)hex-4-yl, 3-(hydroximino)hex-4-yl,1-(hydroximino)-2-ethylbut-3-yl, 1-(hydroximino)-2-ethylbut-4-yl or1-(hydroximino)-2-propylprop-3-yl;

aminocarbonyl-C₁ -C₆ -alkyl is aminocarbonylmethyl,1-(aminocarbonyl)eth-1-yl, 2-(aminocarbonyl)eth-1-yl,1-(aminocarbonyl)prop-1-yl, 2-(aminocarbonyl)prop-1-yl,3-(aminocarbonyl)prop-1-yl, 1-(aminocarbonyl)prop-2-yl,2-(aminocarbonyl)prop-3-yl, 1-(aminocarbonyl)but-1-yl,2-(aminocarbonyl)but-1-yl, 2-(aminocarbonyl)but-1-yl,4-(aminocarbonyl)but-1-yl, 1-(aminocarbonyl)but-2-yl,2-(aminocarbonyl)but-2-yl, 1-(aminocarbonyl)but-3-yl,2-(aminocarbonyl)but-3-yl, 1-(aminocarbonyl)-2-methylprop-3-yl,2-(aminocarbonyl)-2-methylprop-3-yl,3-(aminocarbonyl)-2-methylprop-3-yl, 2-(aminocarbonylmethyl)prop-2-yl,1-(aminocarbonyl)pent-1-yl, 2-(aminocarbonyl)pent-1-yl,3-(aminocarbonyl)pent-1-yl, 4-(aminocarbonyl)pent-1-yl,5-(aminocarbonyl)pent-1-yl, 1-(aminocarbonyl)pent-2-yl,2-(aminocarbonyl)pent-2-yl, 1-(aminocarbonyl)pent-3-yl,2-(aminocarbonyl)pent-3-yl, 1-(aminocarbonyl)pent-4-yl,2-(aminocarbonyl)pent-4-yl, 1-(aminocarbonyl)pent-4-yl,1-(aminocarbonyl)-2-ethylprop-3-yl, 1-(aminocarbonyl)hex-1-yl,2-(aminocarbonyl)hex-1-yl, 3-(aminocarbonyl)hex-1-yl,4-(aminocarbonyl)hex-1-yl, 5-(aminocarbonyl)hex-1-yl,6-(aminocarbonyl)hex-1-yl, 1-(aminocarbonyl)hex-2-yl,2-(aminocarbonyl)hex-2-yl, 1-(aminocarbonyl)hex-3-yl,2-(aminocarbonyl)hex-3-yl, 1-(aminocarbonyl)hex-4-yl,2-(aminocarbonyl)hex-4-yl, 3-(aminocarbonyl)hex-4-yl,1-(aminocarbonyl)-2-ethylbut-3-yl, 1-(aminocarbonyl)-2-ethylbut-4-yl or1-(aminocarbonyl)-2-propylprop-3-yl;

C₁ -C₆ -alkoxy and alkoxy moieties of C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₁-C₆ -alkoxy-C₂ -C₆ -alkyl and di(C₁ -C₆ -alkoxy)-C₁ -C₁ -alkyl are eachmethoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy,2-methylpropoxy or 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexyloxy,1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy,4-methylpentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy,1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyor 1-ethyl-2-methylpropoxy;

C₁ -C₆ -haloalkoxy is C₁ -C₆ -alkoxy as stated above which is partiallyor completely substituted by fluorine, chlorine, bromine and/or iodine,eg. difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy,2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy,3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy,heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy,1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, nonafluorobutoxy,5-fluoropentyloxy, 5-chloropentyloxy, 5-bromopentyloxy, 5-iodopentyloxy,undecafluoropentyloxy, 6-fluorohexyloxy, 6-chlorohexyloxy,6-bromohexyloxy or dodecafluorohexyloxy;

C₁ -C₆ -alkylthio and the alkylthio moieties of C₁ -C₆ -alkylthio-C₁ -C₆-alkyl, C₁ -C₆ -alkylthio-C₂ C₆ -alkyl and di(C₁ -C₆ -alkylthio)-C₁ -C₁-alkyl are each methylthio, ethylthio, n-propylthio, 1-methylethylthio,n-butylthio, 1-methylpropylthio, 2-methylpropylthio,1,1-dimethyl-ethylthio, n-pentylthio, 1-methylbutylthio,2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio,1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio,1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio,3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio,2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;

C₁ -C₆ -haloalkylthio is C₁ -C₆ -alkylthio as stated above which ispartially or completely substituted by fluorine, chlorine, bromineand/or iodine, eg. difluoromethylthio, trifluoromethylthio,chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio,2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2,2-difluoroethylthio, 2,2,-dichloro-2-fluoroethylthio,pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio,3-bromopropylthio, 2,2,-difluoropropylthio, 2,3-difluoropropylthio,2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio,4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio,5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio or6-chlorohexylthio;

(C₁ -C₆ -alkoxy)carbonyl and the alkoxycarbonyl moiety of (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl are each methoxycarbonyl, ethoxycarbonyl,n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl,1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl,1,1-di-methylethoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl,2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexyloxycarbonyl,1-methylpentyloxycarbonyl, 2-methylpentyloxycarbonyl,3-methylpentyloxycarbonyl, 4-methylpentyloxycarbonyl,1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropylcarbonyl;

(C₁ -C₆ -haloalkoxy)carbonyl is (C₁ -C₆ -alkoxy)carbonyl as stated abovewhich is partially or completely substituted by fluorine, chlorineand/or bromine, eg. 2-bromoethoxycarbonyl, 2-chloroethoxycarbonyl,2-fluoroethoxycarbonyl, 2-trifluoromethyl-2-methylethoxycarbonyl or2-trichloromethyl-2-methylethoxycarbonyl;

(C₁ -C₆ -alkyl)carbonyl and the alkylcarbonyl moiety of (C₁ -C₆-alkyl)carbonyl-C₁ -C₆ -alkyl are each methylcarbonyl, ethylcarbonyl,n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl,1-methylpropylcarbonyl, 2-methylpropylcarbonyl,1,1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl,2-methylbutylcarbonyl, 3-methylbutylcarbonyl,1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl,1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl,4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl,1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl,2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl,3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;

(C₁ -C₆ -haloalkyl)carbonyl is (C₁ -C₆ -alkyl)carbonyl as stated abovewhich is partially or completely substituted by fluorine, chlorineand/or bromine, eg. chloroacetyl, dichloroacetyl, trichloroacetyl,fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl,dichlorofluoroacetyl, chlorodifluoroacetyl, 1-fluoropropionyl,2-fluoropropionyl, 2,2-difluoropropionyl, 3,3,3-trifluoropropionyl,3-chloro-3-fluoropropionyl, 3-chloro-3,3-difluoropropionyl,3,3-dichloro-3-fluoropropionyl, trichloropropionyl orpentafluoropropionyl;

aminocarbonyl(C₁ -C₆ -alkyl)carbonyl is aminocarbonylmethylcarbonyl,1-(aminocarbonyl)eth-1-ylcarbonyl, 2-(aminocarbonyl)-eth-1-ylcarbonyl,1-(aminocarbonyl)prop-1-yl-carbonyl, 2-(aminocarbonyl)prop-1-ylcarbonyl,3-(aminocarbonyl)prop-1-ylcarbonyl, 1-(aminocarbonyl)prop-2-ylcarbonyl,2-(aminocarbonyl)prop-2-ylcarbonyl, 1-(aminocarbonyl)but-1-ylcarbonyl,2-(aminocarbonyl)but-1-ylcarbonyl, 3-(aminocarbonyl)but-1-ylcarbonyl,4-(aminocarbonyl)but-1-ylcarbonyl, 1-(aminocarbonyl)but-2-ylcarbonyl,2-(aminocarbonyl)but-2-ylcarbonyl, 1-(aminocarbonyl)but-3-ylcarbonyl,2-(aminocarbonyl)but-3-ylcarbonyl,1-(aminocarbonyl)-2-methylprop-3-ylcarbonyl,2-(aminocarbonyl)-2-methylprop-3-ylcarbonyl,3-(aminocarbonyl)-2-methylprop-3-ylcarbonyl,2-(aminocarbonylmethyl)prop-2-ylcarbonyl,1-(aminocarbonyl)pent-1-ylcarbonyl, 2-(aminocarbonyl)pent-1-ylcarbonyl,3-(aminocarbonyl)pent-1-ylcarbonyl, 4-(aminocarbonyl)pent-1-ylcarbonyl,5-(aminocarbonyl)pent-1-ylcarbonyl, 1-(aminocarbonyl)pent-2-ylcarbonyl,2-(aminocarbonyl)pent-2-ylcarbonyl, 1-(aminocarbonyl)pent-3-ylcarbonyl,2-(aminocarbonyl)pent-3-ylcarbonyl, 1-(aminocarbonyl)pent-4-ylcarbonyl,2-(aminocarbonyl)pent-4-ylcarbonyl, 3-(aminocarbonyl)pent-4-ylcarbonyl,1-(aminocarbonyl)-2-ethylprop-3-ylcarbonyl,1-(aminocarbonyl)hex-1-ylcarbonyl, 2-(aminocarbonyl)hex-1-ylcarbonyl,3-(aminocarbonyl)hex-1-ylcarbonyl, 4-(aminocarbonyl)hex-1-ylcarbonyl,5-(aminocarbonyl)hex-1-ylcarbonyl, 6-(aminocarbonyl)hex-1-ylcarbonyl,1-(aminocarbonyl)hex-2-ylcarbonyl, 2-(aminocarbonyl)hex-2-ylcarbonyl,1-(aminocarbonyl)hex-3-ylcarbonyl, 2-(aminocarbonyl)hex-3-ylcarbonyl,1-(aminocarbonyl)hex-4-ylcarbonyl, 2-(aminocarbonyl)hex-4-ylcarbonyl,3-(aminocarbonyl)hex-4-ylcarbonyl,1-(aminocarbonyl)-2-ethylbut-3-ylcarbonyl,1-(aminocarbonyl)-2-ethylbut-4-yl or1-(aminocarbonyl)-2-propylprop-3-ylcarbonyl;

C₁ -C₄ -alkylimino is methylimino, ethylimino, n-propylimino,1-methylethylimino, n-butylimino, 1-methylpropylimino,2-methylpropylimino or 1,1-dimethylethylimino;

the alkoximino moiety of C₁ -C₆ -alkoximino-C₁ -C₆ -alkyl ismethoximino, ethoximino, 1-propoximino, 2-propoximino,1-methylethoximino, n-butoximino, sec-butoximino, tertbutoximino,1-methyl-1-propoximino, 2-methyl-1-propoximino, 1-methyl-2-propoximino,2-methyl-2-propoximino, n-pentyloximino, 2-pentyloximino,3-pentyloximino, 4-pentyloximino, 1-methyl-1-butoximino,2-methyl-1-butoximino, 3-methyl-1-butoximino, 1-methyl-2-butoximino,2-methyl-2-butoximino, 3-methyl-2-butoximino, 1-methyl-3-butoximino,2-methyl-3-butoximino, 3-methyl-3-butoximino,1,1-dimethyl-2-propoximino, 1,2-dimethyl-1-propoximino,1,2-dimethyl-2-propoximino, 1-ethyl-1-propoximino,1-ethyl-2-propoximino, n-hexyloximino, 2-hexyloximino, 3-hexyloximino,4-hexyloximino, 5-hexyloximino, 1-methyl-1-pentyloximino,2-methyl-1-pentyloximino, 3-methyl-1-pentyloximino,4-methyl-1-pentyloximino, 1-methyl-2-pentyloximino,2-methyl-2-pentyloximino, 3-methyl-2-pentyloximino,4-methyl-2-pentyloximino, 1-methyl-3-pentyloximino,2-methyl-3-pentyloximino, 3-methyl-3-pentyloximino,4-methyl-3-pentyloximino, 1-methyl-4-pentyloximino,2-methyl-4-pentyloximino, 3-methyl-4-pentyloximino,4-methyl-4-pentoximino, 1,1-dimethyl-2-butoximino,1,1-dimethyl-3-butoximino, 1,2-dimethyl-1-butoximino,1,2-dimethyl-2-butoximino, 1,2-dimethyl-3-butoximino,1,3-dimethyl-1-butoximino, 1,3-dimethyl-2-butoximino,1,3-dimethyl-3-butoximino, 2,2-dimethyl-3-butoximino,2,3-dimethyl-1-butoximino, 2,3-dimethyl-2-butoximino,2,3-dimethyl-3-butoximino, 3,3-dimethyl-1-butoximino,3,3-dimethyl-2-butoximino, 1-ethyl-1-butoximino, 1-ethyl-2-butenoximino,1-ethyl-3-butoximino, 2-ethyl-1-butoximino, 2-ethyl-2-butoximino,2-ethyl-3-butoximino, 1,1,2-trimethyl-2-propoximino,1-ethyl-1-methyl-2-propoximino, 1-ethyl-2-methyl-1-propoximino or1-ethyl-2-methyl-2-propoximino;

(C₁ -C₆ -alkylamino)carbonyl and the alkylaminocarbonyl moiety of (C₁-C₆ -alkylamino)carbonyl-C₁ -C₆ -alkyl are each, for example,methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl,1-methylethylaminocarbonyl, n-butylaminocarbonylmethyl,1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl,1,1-dimethylethylaminocarbonyl, n-pentylaminocarbonyl,1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,3-methylbutylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl,2-dimethylpropylaminocarbonyl, 2-dimethylpropylaminocarbonyl,1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl,1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl,3-methylpentylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl,1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl,2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl,1-ethylbutylamino- carbonyl, 2-ethylbutylaminocarbonyl,1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl,1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylaminocarbonyl;

di(C₁ -C₆ -alkyl)aminocarbonyl and the dialkylaminocarbonyl moiety ofdi(C₁ -C₆ -alkyl)aminocarbonyl-C₁ -C₆ -alkyl are each, for example,N,N-dimethylaminocarbonylmethyl, N,N-diethylaminocarbonyl,N,N-diisopropylaminocarbonyl, N,N-dibutylaminocarbonyl,N,N-di-(1-methylpropyl)aminocarbonyl,N,N-di-(2-methylpropyl)aminocarbonyl,N,N-di-(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl,N-methyl-N-propylaminocarbonyl N-methyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-methylaminocarbonyl,N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl,N-ethyl-N-(2-methylpropyl)aminocarbonyl,N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl,N-(1-methylpropyl)-N-propylaminocarbonyl,N-(2-methylpropyl)-N-propylaminocarbonyl,N-(1,1-dimethylethyl)-N-propylaminocarbonyl,N-butyl-N-(1-methylethyl)aminocarbonyl,N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1,-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,N-butyl-N-(1-methylpropyl)aminocarbonyl,N-butyl-N-(2-methylpropyl)aminocarbonyl,N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl orN-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl.

Aryl is to be understood as meaning in particular phenyl or naphthyl.

Hetaryl is preferably to be understood as meaning a 5-membered or6-membered aromatic heterocyclic structure which, if desired, may carrya fused benzene ring. Particularly preferred heteroaromatic structuresare 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,1,3,4-triazol-2-yl, 1,2,3,4-tetrazol-5-yl, 2-pyridyl, 3-pyridyl,4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

In view of the use of the novel compounds of the formula I as herbicidesand/or defoliating/desiccating compounds, the variables preferably havethe following meanings, each alone or in combination:

R¹ is hydrogen or 4-methyl;

R² is hydrogen, fluorine or chlorine;

R³ is a substituent from the group 3.01-3.48 (Table 1):

                  TABLE 1                                                         ______________________________________                                        No.                R.sup.3                                                    ______________________________________                                        3.01               F                                                          3.02               Cl                                                         3.03               Br                                                         3.04               I                                                          3.05               CH.sub.3                                                   3.06               C.sub.2 H.sub.5                                            3.07               n-C.sub.3 H.sub.7                                          3.08               i-C.sub.3 H.sub.7                                          3.09               n-C.sub.4 H.sub.9                                          3.10               i-C.sub.4 H.sub.9                                          3.11               sec-C.sub.4 H.sub.9                                        3.12               t-C.sub.4 H.sub.9                                          3.13               CH.sub.2 F                                                 3.14               CHF.sub.2                                                  3.15               CF.sub.3                                                   3.16               CH.sub.2 Cl                                                3.17               CHCl.sub.2                                                 3.18               CCl.sub.3                                                  3.19               CH.sub.2 Br                                                3.20               CHBr.sub.2                                                 3.21               CH.sub.2 CH.sub.2 F                                        3.22               CH.sub.2 CHF.sub.2                                         3.23               CH.sub.2 CF.sub.3                                          3.24               CHFCH.sub.3                                                3.25               CF.sub.2 CH.sub.3                                          3.26               CF.sub.2 CF.sub.3                                          3.27               CH.sub.2 CH.sub.2 Cl                                       3.28               CH(Cl)CH.sub.3                                             3.29               CH.sub.2 CH.sub.2 Br                                       3.30               C(Br)CH.sub.3                                              3.31               OCH.sub.3                                                  3.32               OCH.sub.2 CH.sub.3                                         3.33               O-n-C.sub.3 H.sub.7                                        3.34               O-i-C.sub.3 H.sub.7                                        3.35               O-n-C.sub.4 H.sub.9                                        3.38               O-i-C.sub.4 H.sub.9                                        3.37               O-sec-C.sub.4 H.sub.9                                      3.38               O-tert-C.sub.4 H.sub.9                                     3.39               O--CHF.sub.2                                               3.40               O--CF.sub.3                                                3.41               O--CH.sub.2 CH.sub.2 F                                     3.42               O--CH.sub.2 CHF.sub.2                                      3.43               O--CH.sub.2 CF.sub.3                                       3.44               O--CF.sub.2 CF.sub.3                                       3.45               O--CH.sub.2 CH.sub.2 Cl                                    3.46               O--CH.sub.2 CH.sub.2 Br                                    3.47               CN                                                         3.48               NO.sub.2                                                   ______________________________________                                    

The radicals 3.01-3.05, 3.15, 3.31, 3.39, 3.40, 3.47 or 3.48 areparticularly preferred, in particular 3.01-3.04 and 3.47;

R⁴ is hydrogen, cyano, nitro, fluorine, chlorine, bromine, iodine,methyl, ethyl, n-propyl or 1-methylethyl, in particular hydrogen, cyano,fluorine, chlorine, bromine or methyl;

R⁵ is a substituent from the group 5.01-5.51 (Table 2):

                  TABLE 2                                                         ______________________________________                                        No.              R.sup.5                                                      ______________________________________                                        5.01             H                                                            5.02             CH.sub.3                                                     5.03             C.sub.2 H.sub.5                                              5.04             n-C.sub.3 H.sub.7                                            5.05             i-C.sub.3 H.sub.7                                            5.06             n-C.sub.4 H.sub.9                                            5.07             i-C.sub.4 H.sub.9                                            5.08             sec-C.sub.4 H.sub.9                                          5.09             tert-C.sub.4 H.sub.9                                         5.10             CH═CH.sub.2                                              5.11             CH.sub.2 --CH═CH.sub.2                                   5.12             CH.sub.2 --CH═CH--CH.sub.3                               5.13             CH═CH.sub.2 --CH.sub.3                                   5.14             C(CH.sub.3)═CH.sub.2                                     5.15             CH═C(CH.sub.3).sub.2                                     5.16             C(CH.sub.3)═CH(CH.sub.3)                                 5.17             CH.sub.2 --CH═C(CH.sub.3).sub.2                          5.18             --C.tbd.CH                                                   5.19             CH.sub.2 --C.tbd.CH                                          5.20             C.tbd.C--CH.sub.3                                            5.21             CH.sub.2 --C.tbd.C--CH.sub.3                                 5.22             CH.sub.2 F                                                   5.23             CH.sub.2 Cl                                                  5.24             CH.sub.2 Br                                                  5.25             CH.sub.2 I                                                   5.26             CHF.sub.2                                                    5.27             CHCl.sub.2                                                   5.28             CHBr.sub.2                                                   5.29             CF.sub.3                                                     5.30             CH(F)CH.sub.3                                                5.31             CH(Cl)CH.sub.3                                               5.32             CH(Br)CH.sub.3                                               5.33             CH(I)CH.sub.3                                                5.34             CH.sub.2 CN                                                  5.35             CH(CH.sub.3)CN                                               5.36             CH.sub.2 CH.sub.2 CN                                         5.37             CH.sub.2 OH                                                  5.38             CH(CH.sub.3)OH                                               5.39             CH.sub.2 OCH.sub.3                                           5.40             CH.sub.2 OC.sub.2 H.sub.5                                    5.41             CH(CH.sub.3)OCH.sub.3                                        5.42             CH(CH.sub.3)OC.sub.2 H.sub.5                                 5.43             CH.sub.2 SH                                                  5.44             CH(CH.sub.3)SH                                               5.45             CH.sub.2 CH.sub.2 SH                                         5.46             CH.sub.2 SCH.sub.3                                           5.47             CH.sub.2 SC.sub.2 H.sub.5                                    5.48             CH(CH.sub.3)SCH.sub.3                                        5.49             CH(CH.sub.3)SC.sub.2 H.sub.5                                 5.50             CH.sub.2 CH.sub.2 SCH.sub.3                                  5.51             CH.sub.2 CH.sub.2 SC.sub.2 H.sub.5                           ______________________________________                                    

R⁶ is a substituent from the group 6.01-6.147 (Table 3):

                  TABLE 3                                                         ______________________________________                                        No.              R.sup.5                                                      ______________________________________                                        6.01             H                                                            6.02             CH.sub.3                                                     6.03             C.sub.2 H.sub.5                                              6.04             n-C.sub.3 H.sub.7                                            6.05             i-C.sub.3 H.sub.7                                            6.06             n-C.sub.4 H.sub.9                                            6.07             i-C.sub.4 H.sub.9                                            6.08             sec-C.sub.4 H.sub.9                                          6.09             tert-C.sub.4 H.sub.9                                         6.10             CH═CH.sub.2                                              6.11             CH.sub.2 --CH═CH.sub.2                                   6.12             CH.sub.2 --CH═CH--CH.sub.3                               6.13             CH═CH.sub.2 --CH.sub.3                                   6.14             C(CH.sub.3)═CH.sub.2                                     6.15             CH═C(CH.sub.3).sub.2                                     6.16             C(CH.sub.3)═CH--CH.sub.3                                 6.17             CH.sub.2 --CH═C(CH.sub.3).sub.2                          6.18             C.tbd.CH                                                     6.19             CH.sub.2 --C.tbd.CH                                          6.20             C.tbd.C--CH.sub.3                                            6.21             CH.sub.2 --C.tbd.C--CH.sub.3                                 6.22             CH.sub.2 F                                                   6.23             CH.sub.2 Cl                                                  6.24             CH.sub.2 Br                                                  6.25             CH.sub.2 I                                                   6.26             CHF.sub.2                                                    6.27             CHCl.sub.2                                                   6.28             CHBr.sub.2                                                   6.29             CF.sub.3                                                     6.30             CH(F)CH.sub.3                                                6.31             CH(Cl)CH.sub.3                                               6.32             CH(Br)CH.sub.3                                               6.33             CH(I)CH.sub.3                                                6.34             CH.sub.2 CN                                                  6.35             CH(CH.sub.3)CN                                               6.36             CH.sub.2 CH.sub.2 CN                                         6.37             CH.sub.2 OH                                                  6.38             CH(CH.sub.3)OH                                               6.39             CH.sub.2 OCH.sub.3                                           6.40             CH.sub.2 OC.sub.2 H.sub.5                                    6.41             CH(CH.sub.3)OCH.sub.3                                        6.42             CH(CH.sub.3)OC.sub.2 H.sub.5                                 6.43             CH.sub.2 SH                                                  6.44             CH(CH.sub.3)SH                                               6.45             CH.sub.2 CH.sub.2 SH                                         6.46             C.sub.2 SCH.sub.3                                            6.47             C.sub.2 SC.sub.2 H.sub.5                                     6.48             CH(CH.sub.3)SCH.sub.3                                        6.49             CH(CH.sub.3)SC.sub.2 H.sub.5                                 6.50             CH.sub.2 CH.sub.2 SCH.sub.3                                  6.51             CH.sub.2 CH.sub.2 SCH.sub.5                                  6.52             cyclopropyl                                                  6.53             cyclobutyl                                                   6.54             cyclopentyl                                                  6.55             cyclohexyl                                                   6.56             CH.sub.2 -cyclopropyl                                        6.57             CH.sub.2 -cyclobutyl                                         6.58             CH.sub.2 -cyclopentyl                                        6.59             CH.sub.2 -cyclohexyl                                         6.60             CH.sub.2 CO.sub.2 H                                          6.61             CH.sub.2 CO.sub.2 CH.sub.3                                   6.62             CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                            6.63             CH.sub.2 CO.sub.2 CH(CH.sub.3).sub.2                         6.64             CH(CH.sub.3)CO.sub.2 H                                       6.65             CH(CH.sub.3)CO.sub.2 CH.sub.3                                6.66             CH(CH.sub.3)CO.sub.2 C.sub.2 H.sub.5                         6.67             CH(CH.sub.3)CO.sub.2 CH(CH.sub.3).sub.2                      6.68             CH.sub.2 CH.sub.2 COOH                                       6.69             CH.sub.2 CH.sub.2 COOCH.sub.3                                6.70             CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                         6.71             CH.sub.2 CH.sub.2 COOCH(CH.sub.3).sub.2                      6.72             CH.sub.2 CONH.sub.2                                          6.73             CH.sub.2 CONHCH.sub.3                                        6.74             CH.sub.2 CON(CH.sub.3).sub.2                                 6.75             CH.sub.2 CONHC.sub.2 H.sub.5                                 6.76             CH.sub.2 CON(C.sub.2 H.sub.5).sub.2                          6.77             CH(CH.sub.3)CONH.sub.2                                       6.78             CH(CH.sub.3)CONHCH.sub.3                                     6.79             CH(CH.sub.3)CON(CH.sub.3).sub.2                              6.80             CH(CH.sub.3)CONHC.sub.2 H.sub.5                              6.81             CH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2                       6.82             CH.sub.2 CH.sub.2 CONH.sub.2                                 6.83             CH.sub.2 CH.sub.2 CONHCH.sub.3                               6.84             CH.sub.2 CH.sub.2 CON(CH.sub.3).sub.2                        6.85             CH.sub.2 CH.sub.2 CONHC.sub.2 H.sub.5                        6.86             CH.sub.2 CH.sub.2 CON(C.sub.2 H.sub.5).sub.2                 6.87             CH.sub.2 COCH.sub.3                                          6.88             CH.sub.2 CH.sub.2 COCH.sub.3                                 6.89             CH.sub.2 CH.sub.2 COC.sub.2 H.sub.5                          6.90             CH.sub.2 C(NOCH.sub.3)H                                      6.91             CH.sub.2 C(NOC.sub.2 H.sub.5)H                               6.92             CH.sub.2 C(NOCH.sub.3)CH.sub.3                               6.93             CH.sub.2 C(NOC.sub.2 H.sub.5)CH.sub.3                        6.94             CH.sub.2 CH.sub.2 C(NOCH.sub.3)H                             6.95             CH.sub.2 CH.sub.2 C(NOCH.sub.3)CH.sub.3                      6.96             CH.sub.2 CH.sub.2 C(NOC.sub.2 H.sub.5)H                      6.97             CH.sub.2 CH.sub.2 C(NOC.sub.2 H.sub.5)CH.sub.3               6.98             CH.sub.2 C(NOH)H                                             6.99             CH.sub.2 C(NOH)CH.sub.3                                      6.100            CH.sub.2 CH.sub.2 C(NOH)H                                    6.101            CH.sub.2 CH.sub.2 C(NOH)CH.sub.3                             6.102            CH.sub.2 CH(OCH.sub.3).sub.2                                 6.103            CH.sub.2 CH(OC.sub.2 H.sub.5).sub.2                          6.104            CH.sub.2 CH(SCH.sub.3).sub.2                                 6.105            CH.sub.2 CH(SC.sub.2 H.sub.5).sub.2                          6.106            CH.sub.2 --C(Cl)═CH.sub.2                                6.107            CH.sub.2 --C(Cl)═CCl.sub.2                               6.108            COOH                                                         6.109            COOCH.sub.3                                                  6.110            COOC.sub.2 H.sub.5                                           6.111            COOCH(CH.sub.3).sub.2                                        6.112            CONH.sub.2                                                   6.113            CONHCH.sub.3                                                 6.114            CON(CH.sub.3).sub.2                                          6.115            CONH(C.sub.2 H.sub.5)                                        6.116            CON(C.sub.2 H.sub.5).sub.2                                   6.117            COCH.sub.3                                                   6.118            COC.sub.2 H.sub.5                                            6.119            COCH(CH.sub.3).sub.2                                         6.120            COCH.sub.2 F                                                 6.121            COCHF.sub.2                                                  6.122            COCF.sub.3                                                   6.123            COCH.sub.2 Cl                                                6.124            COCH.sub.2 Cl                                                6.125            COCCl.sub.3                                                  6.126            COCH.sub.2 Br                                                6.127            C.sub.6 H.sub.5                                              6.128            4-CH.sub.3 --C.sub.6 H.sub.5                                 6.129            CH.sub.2 C.sub.6 H.sub.5                                     6.130            CH.sub.2 --C.sub.10 H.sub.7                                  6.131            CH.sub.2 -(4-Cl--C.sub.6 H.sub.4)                            6.132            CH.sub.2 -(4-OCH3--C.sub.6 H.sub.4)                          6.133            CH.sub.2 -(2-imidazolyl)                                     6.134            CH.sub.2 -(2-thiazolyl)                                      6.135            CH.sub.2 -(4-thiazolyl)                                      6.136            CH.sub.2 -(5-thiazolyl)                                      6.137            OCH.sub.3                                                    6.138            OCH.sub.2 CH.sub.3                                           6.139            OCH(CH.sub.3).sub.2                                          6.140            OCHF.sub.2                                                   6.141            SCH.sub.3                                                    6.142            SCH.sub.2 CH.sub.3                                           6.143            SCH(CH.sub.3).sub.2                                          6.144            SCHF.sub.2                                                   6.145            SCF.sub.3                                                    6.146            CN                                                           6.147            NO.sub.2                                                     ______________________________________                                    

or R⁵ and R⁶ together form a substituent from the group (5+6).01 to(5+6).10 (Table 4):

                  TABLE 4                                                         ______________________________________                                        No.          R.sup.5 + R.sup.6                                                ______________________________________                                        (5+6).01     --(CH.sub.2).sub.2 --                                            (5+6).02     --(CH.sub.2).sub.3 --                                            (5+6).03     --(CH.sub.2).sub.4 --                                            (5+6).04     --(CH.sub.2).sub.5 --                                            (5+6).06     --(CH.sub.2).sub.6 --                                            (5+6).06     --CH.sub.2 --O--                                                 (5+6).07     --CH.sub.2 --O--CH.sub.2 ═CH.sub.2 --                        (5+6).08     --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --                (5+6).09     --CH.sub.2 --CH.sub.2 --NH--CH.sub.2 --CH.sub.2 --               (5+6).10     --CH.sub.2 --CH.sub.2 --N(CH.sub.3)--CH.sub.2 --CH.sub.2         ______________________________________                                                     --                                                           

R⁷ is a substituent from the group 7.01-7.60 (Table 5):

                  TABLE 5                                                         ______________________________________                                        No.          R.sup.7                                                          ______________________________________                                        7.01         H                                                                7.02         CH.sub.3                                                         7.03         C.sub.2 H.sub.3                                                  7.04         n-C.sub.2 H.sub.7                                                7.05         i-C.sub.3 H.sub.7                                                7.06         n-C.sub.4 H.sub.9                                                7.07         i-C.sub.4 H.sub.9                                                7.08         sec-C.sub.4 H.sub.9                                              7.09         tert-C.sub.4 H.sub.9                                             7.10         CH.sub.2 CH═CH.sub.2                                         7.11         CH.sub.2 CH═CH--CH.sub.3                                     7.12         CH(CH.sub.3)CH═CH.sub.2                                      7.13         CH.sub.2 --C.tbd.CH                                              7.14         CH(CH.sub.3)--C.tbd.CH                                           7.15         CH.sub.2 --C.tbd.C--CH.sub.3                                     7.16         CHF.sub.2                                                        7.17         CH.sub.2 CH.sub.2 F                                              7.18         CH.sub.2 CH.sub.2 Cl                                             7.19         CH.sub.2 CF.sub.2 H                                              7.20         CH.sub.2 CF.sub.3                                                7.21         CH.sub.2 CCl.sub.3                                               7.22         CH.sub.2 CN                                                      7.23         CH(CH.sub.3)CN                                                   7.24         CH.sub.2 CH.sub.2 OCH.sub.3                                      7.25         CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                             7.26         CH.sub.2 CH.sub.2 SCH.sub.3                                      7.27         CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                             7.28         CH.sub.2 CO.sub.2 CH.sub.3                                       7.29         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                              7.30         CH.sub.2 CO.sub.2 CH(CH.sub.3).sub.2                             7.31         CH(CH.sub.3)CO.sub.2 CH.sub.3                                    7.32         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                           7.33         CH(CH.sub.2 CH.sub.3)CO.sub.2 CH.sub.3                           7.34         CH(CH.sub.2 CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                  7.35         cyclopropyl                                                      7.36         cyclopentyl                                                      7.37         cyclohexyl                                                       7.38         CH.sub.2 -cyclopropyl                                            7.39         CH.sub.2 -cyclopentyl                                            7.40         CH.sub.2 -cyclohexyl                                             7.41         phenyl                                                           7.42         2-F-phenyl                                                       7.43         3-F-phenyl                                                       7.44         4-F-phenyl                                                       7.45         2-Cl-phenyl                                                      7.46         3-Cl-phenyl                                                      7.47         4-Cl-phenyl                                                      7.48         2-CH.sub.3 -phenyl                                               7.49         3-CH.sub.3 -phenyl                                               7.50         4-CH.sub.3 -phenyl                                               7.51         2-CF.sub.3 -phenyl                                               7.52         3-CF.sub.3 -phenyl                                               7.53         4-CF.sub.3 -phenyl                                               7.54         2-CH.sub.3 O-phenyl                                              7.55         3-CH.sub.3 O-phenyl                                              7.56         4-CH.sub.3 O-phenyl                                              7.57         2-CO.sub.2 CH.sub.3 -phenyl                                      7.58         3-CO.sub.2 CH.sub.3 -phenyl                                      7.59         4-CO.sub.2 CH.sub.3 -phenyl                                      7.60         CH.sub.2 -phenyl                                                 ______________________________________                                    

is oxygen or --N(R⁸)--;

R⁸ is a substituent from the group 8.01-8.40 (Table 6)

                  TABLE 6                                                         ______________________________________                                        No.              R.sup.8                                                      ______________________________________                                        8.01             H                                                            8.02             CH.sub.3                                                     8.03             C.sub.2 H.sub.5                                              8.04             n-C.sub.3 H.sub.7                                            8.05             i-C.sub.3 H.sub.7                                            8.06             n-C.sub.4 H.sub.9                                            8.07             CH.sub.2 CH═CH.sub.2                                     8.08             CH.sub.2 CH═CH(CH.sub.3)                                 8.09             CH(CH.sub.3)CH═CH.sub.2                                  8.10             CH.sub.2 C.tbd.CH                                            8.11             CH(CH.sub.3)C.tbd.CH                                         8.12             CH.sub.2 C.tbd.C--CH.sub.3                                   8.13             CH.sub.2 CH.sub.2 F                                          8.14             CH.sub.2 CH.sub.2 Cl                                         8.15             CH.sub.2 CN                                                  8.16             CH(CH.sub.3)CN                                               8.17             CH.sub.2 CH.sub.2 OCH.sub.3                                  8.18             CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                         8.19             CH.sub.2 COOCH.sub.3                                         8.20             CH.sub.2 COOC.sub.2 H.sub.5                                  8.21             CH(CH.sub.3)COOCH.sub.3                                      8.22             CH(CH.sub.3)COOC.sub.2 H.sub.5                               8.23             cyclopropyl                                                  8.24             cyclopentyl                                                  8.25             cyclohexyl                                                   8.26             phenyl                                                       8.27             benzyl                                                       8.28             CO--OCH.sub.3                                                8.29             CO--OC.sub.2 H.sub.5                                         8.30             CO--OCF.sub.3                                                8.31             CO--OC(CH.sub.3).sub.2 --CCl.sub.3                           8.32             CO--CH.sub.3                                                 8.33             CO--C.sub.2 H.sub.5                                          8.34             CO-(n-C.sub.3 H.sub.7)                                       8.35             CO--CF.sub.3                                                 8.36             CO--CH.sub.2 Cl                                              8.37             CO--CH.sub.2 F                                               8.38             Si(CH.sub.3).sub.3                                           8.39             Si(C.sub.2 H.sub.5).sub.3                                    8.40             CO--O-benzyl                                                 ______________________________________                                    

or R⁶ and R⁸ together form one of the following chains: --CH₂ --CH₂--CH₂ --, --CH₂ --CH₂ --CH₂ --CH₂, --CO--CH₂ --CH₂ --, --CO--CH₂ --CH₂--CH₂ --, --CH₂ --CH₂ --O--CH₂, --CH₂ --CH₂ --NH--CH₂ -- or --CH₂ --CH₂--N(CH₃)--CH₂ --.

In view of the use of the substituted phthalimidocinnamic acidderivatives I as herbicides, the compounds Ia (=I where R³ is chlorine,R¹, R⁵ and R⁶ are each hydrogen and X is oxygen) stated in Table 7 arevery particularly preferred:

                  TABLE 7                                                         ______________________________________                                         ##STR3##                                                                     No.        R.sup.2  R.sup.4  R.sup.7                                          ______________________________________                                        Ia.001     H        H        H                                                Ia.002     F        H        H                                                Ia.003     Cl       H        H                                                Ia.004     H        Cl       H                                                Ia.005     F        Cl       H                                                Ia.006     Cl       Cl       H                                                Ia.007     H        Br       H                                                Ia.008     F        Br       H                                                Ia.009     Cl       Br       H                                                Ia.010     H        CH.sub.3 H                                                Ia.011     F        CH.sub.3 H                                                Ia.012              CH.sub.3 H                                                Ia.013              CN       H                                                Ia.014     F        CN       H                                                Ia.015     Cl       CN       H                                                Ia.016     H        H        CH.sub.3                                         Ia.017     F        H        CH.sub.3                                         Ia.018     Cl       H        CH.sub.3                                         Ia.019     H        Cl       CH.sub.3                                         Ia.020     F        Cl       CH.sub.3                                         Ia.021     Cl       Cl       CH.sub.3                                         Ia.022     H        Br       CH.sub.3                                         Ia.023     F        Br       CH.sub.3                                         Ia.024     Cl       Br       CH.sub.3                                         Ia.025     H        CH.sub.3 CH.sub.3                                         Ia.026     F        CH.sub.3 CH.sub.3                                         Ia.027     Cl       CH.sub.3 CH.sub.3                                         Ia.028     H        CN       CH.sub.3                                         Ia.029     F        CN       CH.sub.3                                         Ia.030     Cl       CN       CH.sub.3                                         Ia.031     H        H        C.sub.2 H.sub.5                                  Ia.032     F        H        C.sub.2 H.sub.5                                  Ia.033     Cl       H        C.sub.2 H.sub.5                                  Ia.034     H        Cl       C.sub.2 H.sub.5                                  Ia.035     F        Cl       C.sub.2 H.sub.5                                  Ia.036     Cl       Cl       C.sub.2 H.sub.5                                  Ia.037     H        Br       C.sub.2 H.sub.5                                  Ia.038     F        Br       C.sub.2 H.sub.5                                  Ia.039     Cl       Br       C.sub.2 H.sub.5                                  Ia.040     H        CH.sub.3 C.sub.2 H.sub.5                                  Ia.041     F        CH.sub.3 C.sub.2 H.sub.5                                  Ia.042     Cl       CH.sub.3 C.sub.2 H.sub.5                                  Ia.043     H        CN       C.sub.2 H.sub.5                                  Ia.044     F        CN       C.sub.2 H.sub.5                                  Ia.045     Cl       CN       C.sub.2 H.sub.5                                  Ia.046     H        H        CH.sub.2 CH.sub.2 CH.sub.3                       Ia.047     F        H        CH.sub.2 CH.sub.2 CH.sub.3                       Ia.048     Cl       H        CH.sub.2 CH.sub.2 CH.sub.3                       Ia.049     H        Cl       CH.sub.2 CH.sub.2 CH.sub.3                       Ia.050     F        Cl       CH.sub.2 CH.sub.2 CH.sub.3                       Ia.051     Cl       Cl       CH.sub.2 CH.sub.2 CH.sub.3                       Ia.052     H        Br       CH.sub.2 CH.sub.2 CH.sub.3                       Ia.053     F        Br       CH.sub.2 CH.sub.2 CH.sub.3                       Ia.054     Cl       Br       CH.sub.2 CH.sub.2 CH.sub.3                       Ia.055     H        CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                       Ia.056     F        CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                       Ia.057     Cl       CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3                       Ia.058     H        CN       CH.sub.2 CH.sub.2 CH.sub.3                       Ia.059     F        CN       CH.sub.2 CH.sub.2 CH.sub.3                       Ia.060     Cl       CN       CH.sub.2 CH.sub.2 CH.sub.3                       Ia.061     H        H        CH(CH.sub.3).sub.2                               Ia.062     F        H        CH(CH.sub.3).sub.2                               Ia.063     Cl       H        CH(CH.sub.3).sub.2                               Ia.064     H        Cl       CH(CH.sub.3).sub.2                               Ia.065     F        Cl       CH(CH.sub.3).sub.2                               Ia.066     Cl       Cl       CH(CH.sub.3).sub.2                               Ia.067     H        Br       CH(CH.sub.3).sub.2                               Ia.068     F        Br       CH(CH.sub.3).sub.2                               Ia.069     Cl       Br       CH(CH.sub.3).sub.2                               Ia.070     H        CH.sub.3 CH(CH.sub.3).sub.2                               Ia.071     F        CH.sub.3 CH(CH.sub.3).sub.2                               Ia.072     Cl       CH.sub.3 CH(CH.sub.3).sub.2                               Ia.073     H        CN       CH(CH.sub.3).sub.2                               Ia.074     F        CN       CH(CH.sub.3).sub.2                               Ia.075     Cl       CN       CH(CH.sub.3).sub.2                               Ia.076     H        H        CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.077     F        H        CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.078     Cl       H        CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.079     H        Cl       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.080     F        Cl       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.081     Cl       Ci       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.082     H        Br       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.083     F        Br       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.084     Cl       Br       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.085     H        CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.086     F        CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.087     Cl       CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.088     H        CN       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.089     F        CN       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.090     Cl       CN       CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3              Ia.091     H        H        CH.sub.2 CH(CH.sub.3).sub.2                      Ia.092     F        H        CH.sub.2 CH(CH.sub.3).sub.2                      Ia.093     Cl       H        CH.sub.2 CH(CH.sub.3).sub.2                      Ia.094     H        Cl       CH.sub.2 CH(CH.sub.3).sub.2                      Ia.095     F        Cl       CH.sub.2 CH(CH.sub.3).sub.2                      Ia.096     Ci       Cl       CH.sub.2 CH(CH.sub.3).sub.2                      Ia.097     H        Br       CH.sub.2 CH(CH.sub.3).sub.2                      Ia.098     F        Br       CH.sub.2 CH(CH.sub.3).sub.2                      Ia.099     Cl       Br       CH.sub.2 CH(CH.sub.3).sub.2                      Ia.100     H        CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2                      Ia.101     F        CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2                      Ia.102     Cl       CH.sub.3 CH.sub.2 CH(CH.sub.3).sub.2                      Ia.103     H        CN       CH.sub.2 CH(CH.sub.3).sub.2                      Ia.104     F        CN       CH.sub.2 CH(CH.sub.3).sub.2                      Ia.105     Cl       CN       CH.sub.2 CH(CH.sub.3).sub.2                      Ia.106     H        H        C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.107     F        H        C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.108     Cl       H        C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.109     H        Cl       C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.110     F        Cl       C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.111     Cl       Cl       C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.112     H        Br       C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.113     F        Br       C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.114     Cl       Br       C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.115     H        CH.sub.3 C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.116     F        CH.sub.3 C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.117     Cl       CH.sub.3 C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.118     H        CN       C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.119     F        CN       C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.120     Cl       CN       C(CH.sub.3)CH.sub.2 CH.sub.3                     Ia.121     H        H        C(CH.sub.3).sub.3                                Ia.122     F        H        C(CH.sub.3).sub.3                                Ia.123     Cl       H        C(CH.sub.3).sub.3                                Ia.124     H        Cl       C(CH.sub.3).sub.3                                Ia.125     F        Cl       C(CH.sub.3).sub.3                                Ia.126     Cl       Cl       C(CH.sub.3).sub.3                                Ia.127     H        Br       C(CH.sub.3).sub.3                                Ia.128     F        Br       C(CH.sub.3).sub.3                                Ia.129     Cl       Br       C(CH.sub.3).sub.3                                Ia.130     H        CH.sub.3 C(CH.sub.3).sub.3                                Ia.131     F        CH.sub.3 C(CH.sub.3).sub.3                                Ia.132     Cl       CH.sub.3 C(CH.sub.3).sub.3                                Ia.133     H        CN       C(CH.sub.3).sub.3                                Ia.134     F        CN       C(CH.sub.3).sub.3                                Ia.135     Cl       CN       C(CH.sub.3).sub.3                                Ia.136     H        H        CH.sub.2 CHCH.sub.2                              Ia.137     F        H        CH.sub.2 CHCH.sub.2                              Ia.138     Cl       H        CH.sub.2 CHCH.sub.2                              Ia.139     H        Cl       CH.sub.2 CHCH.sub.2                              Ia.140     F        Cl       CH.sub.2 CHCH.sub.2                              Ia.141     Cl       Cl       CH.sub.2 CHCH.sub.2                              Ia.142     H        Br       CH.sub.2 CHCH.sub.2                              Ia.143     F        Br       CH.sub.2 CHCH.sub.2                              Ia.144     Cl       Br       CH.sub.2 CHCH.sub.2                              Ia.145     H        CH.sub.3 CH.sub.2 CHCH.sub.2                              Ia.146     F        CH.sub.3 CH.sub.2 CHCH.sub.2                              Ia.147     Cl       CH.sub.3 CH.sub.2 CHCH.sub.2                              Ia.148     H        CN       CH.sub.2 CHCH.sub.2                              Ia.149     F        CN       CH.sub.2 CHCH.sub.2                              Ia.150     Cl       CN       CH.sub.2 CHCH.sub.2                              Ia.151     H        H        CH.sub.2 CHCH (CH.sub.3)                         Ia.152     F        H        CH.sub.2 CHCH(CH.sub.3)                          Ia.153     Cl       H        CH.sub.2 CHCH(CH.sub.3)                          Ia.154     H        Cl       CH.sub.2 CHCH(CH.sub.3)                          Ia.155     F        Cl       CH.sub.2 CHCH(CH.sub.3)                          Ia.156     Cl       Cl       CH.sub.2 CHCH(CH.sub.3)                          Ia.157     H        Br       CH.sub.2 CHCH(CH.sub.3)                          Ia.158     F        Br       CH.sub.2 CHCH(CH.sub.3)                          Ia.159     Cl       Br       CH.sub.2 CHCH(CH.sub.3)                          Ia.160     H        CH.sub.3 CH.sub.2 CHCH(CH.sub.3)                          Ia.161     F        CH.sub.3 CH.sub.2 CHCH(CH.sub.3)                          Ia.162     Cl       CH.sub.3 CH.sub.2 CHCH(CH.sub.3)                          Ia.163     H        CN       CH.sub.2 CHCH(CH.sub.3)                          Ia.164     F        CN       CH.sub.2 CHCH(CH.sub.3)                          Ia.165     Cl       CN       CH.sub.2 CHCH(CH.sub.3)                          Ia.166     H        H        CH(CH.sub.3)CHCH.sub.2                           Ia.167     F        H        CH(CH.sub.3)CHCH.sub.2                           Ia.168     Cl       H        CH(CH.sub.3)CHCH.sub.2                           Ia.169     H        Cl       CH(CH.sub.3)CHCH.sub.2                           Ia.170     F        Cl       CH(CH.sub.3)CHCH.sub.2                           Ia.171     Cl       Cl       CH(CH.sub.3)CHCH.sub.2                           Ia.172     H        Br       CH(CH.sub.3)CHCH.sub.2                           Ia.173     F        Br       CH(CH.sub.3)CHCH.sub.2                           Ia.174     Cl       Br       CH(CH.sub.3)CHCH.sub.2                           Ia.175     H        CH.sub.3 CH(CH.sub.3)CHCH.sub.2                           Ia.176     F        CH.sub.3 CH(CH.sub.3)CHCH.sub.2                           Ia.177     Cl       CH.sub.3 CH(CH.sub.3)CHCH.sub.2                           Ia.178     H        CN       CH(CH.sub.3)CHCH.sub.2                           Ia.179     F        CN       CH(CH.sub.3)CHCH.sub.2                           Ia.180     Cl       CN       CH(CH.sub.3)CHCH.sub.2                           Ia.181     H        H        CH.sub.2 CCH                                     Ia.182     F        H        CH.sub.2 CCH                                     Ia.183     Cl       H        CH.sub.2 CCH                                     Ia.184     H        Cl       CH.sub.2 CCH                                     Ia.185     F        Cl       CH.sub.2 CCH                                     Ia.186     Cl       Cl       CH.sub.2 CCH                                     Ia.187     H        Br       CH.sub.2 CCH                                     Ia.188     F        Br       CH.sub.2 CCH                                     Ia.189     Cl       Br       CH.sub.2 CCH                                     Ia.190     H        CH.sub.3 CH.sub.2 CCH                                     Ia.191     F        CH.sub.3 CH.sub.2 CCH                                     Ia.192     Cl       CH.sub.3 CH.sub.2 CCH                                     Ia.193     H        CN       CH.sub.2 CCH                                     Ia.194     F        CN       CH.sub.2 CCH                                     Ia.195     Cl       CN       CH.sub.2 CCH                                     Ia.196     H        H        CH(CH.sub.3)CCH                                  Ia.197     F        H        CH(CH.sub.3)CCH                                  Ia.198     Cl       H        CH(CH.sub.3)CCH                                  Ia.199     H        Cl       CH(CH.sub.3)CCH                                  Ia.200     F        Cl       CH(CH.sub.3)CCH                                  Ia.201     Cl       Cl       CH(CH.sub.3)CCH                                  Ia.202     H        Br       CH(CH.sub.3)CCH                                  Ia.203     F        Br       CH(CH.sub.3)CCH                                  Ia.204     Cl       Br       CH(CH.sub.3)CCH                                  Ia.205     H        CH.sub.3 CH(CH.sub.3)CCH                                  Ia.206     F        CH.sub.3 CH(CH.sub.3)CCH                                  Ia.207     Cl       CH.sub.3 CH(CH.sub.3)CCH                                  Ia.208     H        CN       CH(CH.sub.3)CCH                                  Ia.209     F        CN       CH(CH.sub.3)CCH                                  Ia.210     Cl       CN       CH(CH.sub.3)CCH                                  Ia.211     H        H        CH.sub.2 CCCH.sub.3                              Ia.212     F        H        CH.sub.2 CCCH.sub.3                              Ia.213     Cl       H        CH.sub.2 CCCH.sub.3                              Ia.214     H        Cl       CH.sub.2 CCCH.sub.3                              Ia.215     F        Cl       CH.sub.2 CCCH.sub.3                              Ia.216     Cl       Cl       CH.sub.2 CCCH.sub.3                              Ia.217     H        Br       CH.sub.2 CCCH.sub.3                              Ia.218     F        Br       CH.sub.2 CCCH.sub.3                              Ia.219     Cl       Br       CH.sub.2 CCCH.sub.3                              Ia.220     H        CH.sub.3 CH.sub.2 CCCH.sub.3                              Ia.221     F        CH.sub.3 CH.sub.2 CCCH.sub.3                              Ia.222     Cl       CH.sub.3 CH.sub.2 CCCH.sub.3                              Ia.223     H        CN       CH.sub.2 CCCH.sub.3                              Ia.224     F        CN       CH.sub.2 CCCH.sub.3                              Ia.225     Cl       CN       CH.sub.2 CCCH.sub.3                              Ia.226     H        H        CHF.sub.2                                        Ia.227     F        H        CHF.sub.2                                        Ia.228     Cl       H        CHF.sub.2                                        Ia.229     H        Cl       CHF.sub.2                                        Ia.230     F        Cl       CHF.sub.2                                        Ia.231     Cl       Cl       CHF.sub.2                                        Ia.232     H        Br       CHF.sub.2                                        Ia.233     F        Br       CHF.sub.2                                        Ia.234     Cl       Br       CHF.sub.2                                        Ia.235     H        CH.sub.3 CHF.sub.2                                        Ia.236     F        CH.sub.3 CHF.sub.2                                        Ia.237     Cl       CH.sub.3 CHF.sub.2                                        Ia.238     H        CN.      CHF.sub.2                                        Ia.239     F        CN       CHF.sub.2                                        Ia.240     CL       CN       CHF.sub.2                                        Ia.241     H        H        CH.sub.2 CH.sub.2 F                              Ia.242     F        H        CH.sub.2 CH.sub.2 F                              Ia.243     Cl       H        CH.sub.2 CH.sub.2 F                              Ia.244     H        Cl       CH.sub.2 CH.sub.2 F                              Ia.245     F        Cl       CH.sub.2 CH.sub.2 F                              Ia.246     Cl       Cl       CH.sub.2 CH.sub.2 F                              Ia.247     H        Br       CH.sub.2 CH.sub.2 F                              Ia.248     F        Br       CH.sub.2 CH.sub.2 F                              Ia.249     Cl       Br       CH.sub.2 CH.sub.2 F                              Ia.250     H        CH.sub.3 CH.sub.2 CH.sub.2 F                              Ia.251     F        CH.sub.3 CH.sub.2 CH.sub.2 F                              Ia.252     Cl       CH.sub.3 CH.sub.2 CH.sub.2 F                              Ia.253     H        CN       CH.sub.2 CH.sub.2 F                              Ia.254     F        CN       CH.sub.2 CH.sub.2 F                              Ia.255     Cl       CN       CH.sub.2 CH.sub.2 F                              Ia.256     H        H        CH.sub.2 CH.sub.2 Cl                             Ia.257     F        H        CH.sub.2 CH.sub.2 Cl                             Ia.258     Cl       H        CH.sub.2 CH.sub.2 Cl                             Ia.259     H        Cl       CH.sub.2 CH.sub.2 Cl                             Ia.260     F        Cl       CH.sub.2 CH.sub.2 Cl                             Ia.261     Cl       Cl       CH.sub.2 CH.sub.2 Cl                             Ia.262     H        Br       CH.sub.2 CH.sub.2 Cl                             Ia.263     F        Br       CH.sub.2 CH.sub.2 Cl                             Ia.264     Cl       Br       CH.sub.2 CH.sub.2 Cl                             Ia.265     H        CH.sub.3 CH.sub.2 CH.sub.2 Cl                             Ia.266     F        CH.sub.3 CH.sub.2 CH.sub.2 Cl                             Ia.267     Cl       CH.sub.3 CH.sub.2 CH.sub.2 Cl                             Ia.268     H        CN       CH.sub.2 CH.sub.2 Cl                             Ia.269     F        CN       CH.sub.2 CH.sub.2 Cl                             Ia.270     Cl       CN       CH.sub.2 CH.sub.2 Cl                             Ia.271     H        H        CH.sub.2 CF.sub.3                                Ia.272     F        H        CH.sub.2 CF.sub.3                                Ia.273     Cl       H        CH.sub.2 CF.sub.3                                Ia.274     H        Cl       CH.sub.2 CF.sub.3                                Ia.275     F        Cl       CH.sub.2 CF.sub.3                                Ia.276     Cl       Cl       CH.sub.2 CF.sub.3                                Ia.277     H        Br       CH.sub.2 CF.sub.3                                Ia.278     F        Br       CH.sub.2 CF.sub.3                                Ia.279     Cl       Br       CH.sub.2 CF.sub.3                                Ia.280     H        CH.sub.3 CH.sub.2 CF.sub.3                                Ia.281     F        CH.sub.3 CH.sub.2 CF.sub.3                                Ia.282     Cl       CH.sub.3 CH.sub.2 CF.sub.3                                Ia.283     H        CN       CH.sub.2 CF.sub.3                                Ia.284     F        CN       CH.sub.2 CF.sub.3                                Ia.285     Cl       CN       CH.sub.2 CF.sub.3                                Ia.286     H        H        CH.sub.2 CCl.sub.3                               Ia.287     F        H        CH.sub.2 CCl.sub.3                               Ia.288     Cl       H        CH.sub.2 CCl.sub.3                               Ia.289     H        Cl       CH.sub.2 CCl.sub.3                               Ia.290     F        Cl       CH.sub.2 CCl.sub.3                               Ia.291     Cl       Cl       CH.sub.2 CCl.sub.3                               Ia.292     H        Br       CH.sub.2 CCl.sub.3                               Ia.293     F        Br       CH.sub.2 CCl.sub.3                               Ia.294     Cl       Br       CH.sub.2 CCl.sub.3                               Ia.295     H        CH.sub.3 CH.sub.2 CCl.sub.3                               Ia.296     F        CH.sub.3 CH.sub.2 CCl.sub.3                               Ia.297     Cl       CH.sub.3 CH.sub.2 CCl.sub.3                               Ia.298     H        CN       CH.sub.2 CCl.sub.3                               Ia.299     F        CN       CH.sub.2 CCl.sub.3                               Ia.300     Cl       CN       CH.sub.2 CCl.sub.3                               Ia.301     H        H        CH.sub.2 CN                                      Ia.302     F        H        CH.sub.2 CN                                      Ia.303     Cl       H        CH.sub.2 CN                                      Ia.304     H        Cl       CH.sub.2 CN                                      Ia.305     F        Cl       CH.sub.2 CN                                      Ia.306     Cl       Cl       CH.sub.2 CN                                      Ia.307     H        Br       CH.sub.2 CN                                      Ia.308     F        Br       CH.sub.2 CN                                      Ia.309     Cl       Br       CH.sub.2 CN                                      Ia.310     H        CH.sub.3 CH.sub.2 CN                                      Ia.311     F        CH.sub.3 CH.sub.2 CN                                      Ia.312     Cl       CH.sub.3 CH.sub.2 CN                                      Ia.313     H        CN       CH.sub.2 CN                                      Ia.314     F        CN       CH.sub.2 CN                                      Ia.315     Cl       CN       CH.sub.2 CN                                      Ia.316     H        H        CH(CH.sub.3)CN                                   Ia.317     F        H        CH(CH.sub.3)CN                                   Ia.318     Cl       H        CH(CH.sub.3)CN                                   Ia.319     H        Cl       CH(CH.sub.3)CN                                   Ia.320     F        Cl       CH(CH.sub.3)CN                                   Ia.321     Cl       Cl       CH(CH.sub.3)CN                                   Ia.322     H        Br       CH(CH.sub.3)CN                                   Ia.323     F        Br       CH(CH.sub.3)CN                                   Ia.324     Cl       Br       CH(CH.sub.3)CN                                   Ia.325     H        CH.sub.3 CH(CH.sub.3)CN                                   Ia.326     F        CH.sub.3 CH(CH.sub.3)CN                                   Ia.327     Cl       CH.sub.3 CH(CH.sub.3)CN                                   Ia.328     H        CN       CH(CH.sub.3)CN                                   Ia.329     F        CN       CH(CH.sub.3)CN                                   Ia.330     Cl       CN       CH(CH.sub.3)CN                                   Ia.331     H        H        CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.332     F        H        CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.333     Cl       H        CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.334     H        Cl       CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.335     F        Cl       CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.336     Cl       Cl       CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.337     H        Br       CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.338     F        Br       CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.339     Cl       Br       CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.340     H        CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.341     F        CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.342     Cl       CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.343     H        CN       CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.344     F        CN       CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.345     Cl       CN       CH.sub.2 CH.sub.2 OCH.sub.3                      Ia.346     H        H        CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5               Ia.347     F        H        CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5               Ia.348     Cl       H        CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.349     H        Cl       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.350     F        Cl       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.351     Cl       Cl       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.352     H        Br       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.353     F        Br       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.354     Cl       Br       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.355     H        CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.356     F        CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.357     Cl       CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.358     H        CN       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.359     F        CN       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.360     Cl       CN       CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3             Ia.361     H        H        CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.362     F        H        CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.363     Cl       H        CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.364     H        Cl       CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.365     F        Cl       CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.366     Cl       Cl       CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.367     H        Br       CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.368     F        Br       CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.369     Cl       Br       CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.370     H        CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.371     F        CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.372     Cl       CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.373     H        CN       CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.374     F        CN       CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.375     Cl       CN       CH.sub.2 CH.sub.2 SCH.sub.3                      Ia.376     H        H        CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.377     F        H        CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.378     Cl       H        CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.379     H        Cl       CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.380     F        Cl       CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.381     Cl       Cl       CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.382     H        Br       CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.383     F        Br       CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.384     Cl       Br       CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.385     H        CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.386     F        CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.387     Cl       CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.388     H        CN       CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.389     F        CN       CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.390     Cl       CN       CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3             Ia.391     H        H        CH.sub.2 CO.sub.2 CH.sub.3                       Ia.392     F        H        CH.sub.2 CO.sub.2 CH.sub.3                       Ia.393     Cl       H        CH.sub.2 CO.sub.2 CH.sub.3                       Ia.394     H        Cl       CH.sub.2 CO.sub.2 CH.sub.3                       Ia.395     F        Cl       CH.sub.2 CO.sub.2 CH.sub.3                       Ia.396     Cl       Cl       CH.sub.2 CO.sub.2 CH.sub.3                       Ia.397     H        Br       CH.sub.2 CO.sub.2 CH.sub.3                       Ia.398     F        Br       CH.sub.2 CO.sub.2 CH.sub.3                       Ia.399     Cl       Br       CH.sub.2 CO.sub.2 CH.sub.3                       Ia.400     H        CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3                       Ia.401     F        CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3                       Ia.402     Cl       CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3                       Ia.403     H        CN       CH.sub.2 CO.sub.2 CH.sub.3                       Ia.404     F        CN       CH.sub.2 CO.sub.2 CH.sub.3                       Ia.405     Cl       CN       CH.sub.2 CO.sub.2 CH.sub.3                       Ia.406     H        H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.407     F        H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.408     Cl       H        CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.409     H        Cl       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.410     F        Cl       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.411     Cl       Cl       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.412     H        Br       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.413     F        Br       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.414     Cl       Br       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.415     H        CH.sub.3 CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.416     F        CH.sub.3 CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.417     Cl       CH.sub.3 CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.418     H        CN       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.419     F        CN       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.420     Cl       CN       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3           Ia.421     H        H        cyclopropyl                                      Ia.422     F        H        cyclopropyl                                      Ia.423     Cl       H        cyclopropyl                                      Ia.424     H        Cl       cyclopropyl                                      Ia.425     F        Cl       cyclopropyl                                      Ia.426     Cl       Cl       cyclopropyl                                      Ia.427     H        Br       cyclopropyl                                      Ia.428     F        Br       cyclopropyl                                      Ia.429     Cl       Br       cyclopropyl                                      Ia.430     H        CH.sub.3 cyclopropyl                                      Ia.431     F        CH.sub.3 cyclopropyl                                      Ia.432     Cl       CH.sub.3 cyclopropyl                                      Ia.433     H        CN       cyclopropyl                                      Ia.434     F        CN       cyclopropyl                                      Ia.435     Cl       CN       cyclopropyl                                      Ia.436     H        H        CH.sub.2 -cyclopropyl                            Ia.437     F        H        CH.sub.2 -cyclopropyl                            Ia.438     Cl       H        CH.sub.2 -cyclopropyl                            Ia.439     H        Cl       CH.sub.2 -cyclopropyl                            Ia.440     F        Cl       CH.sub.2 -cyclopropyl                            Ia.441     Cl       Cl       CH.sub.2 -cyclopropyl                            Ia.442     H        Br       CH.sub.2 -cyclopropyl                            Ia.443     F        Br       CH.sub.2 -cyclopropyl                            Ia.444     Cl       Br       CH.sub.2 -cyclopropyl                            Ia.445     H        CH.sub.3 CH.sub.2 -cyclopropyl                            Ia.446     F        CH.sub.3 CH.sub.2 -cyclopropyl                            Ia.447     Cl       CH.sub.3 CH.sub.2 -cyclopropyl                            Ia.448     H        CN       CH.sub.2 -cyclopropyl                            Ia.449     F        CN       CH.sub.2 -cyclopropyl                            Ia.450     Cl       CN       CH.sub.2 -cyclopropyl.                           Ia.451     H        H        phenyl                                           Ia.452     F        H        phenyl                                           Ia.453     Cl       H        phenyl                                           Ia.454     H        Cl       phenyl                                           Ia.455     F        Cl       phenyl                                           Ia.456     Cl       Cl       phenyl                                           Ia.457     H        Br       phenyl                                           Ia.458     F        Br       phenyl                                           Ia.459     Cl       Br       phenyl                                           Ia.460     H        CH.sub.3 phenyl                                           Ia.461     F        CH.sub.3 phenyl                                           Ia.462     Cl       CH.sub.3 phenyl                                           Ia.463     H        CN       phenyl                                           Ia.464     F        CN       phenyl                                           Ia.465     Cl       CN       phenyl                                           Ia.466     H        H        2-F-phenyl                                       Ia.467     F        H        2-F-phenyl                                       Ia.468     Cl       H        2-F-phenyl                                       Ia.469     H        Cl       2-F-phenyl                                       Ia.470     F        Cl       2-F-phenyl                                       Ia.471     Cl       Cl       2-F-phenyl                                       Ia.472     H        Br       2-F-phenyl                                       Ia.473     F        Br       2-F-phenyl                                       Ia.474     Cl       Br       2-F-phenyl                                       Ia.475     H        CH.sub.3 2-F-phenyl                                       Ia.476     F        CH.sub.3 2-F-phenyl                                       Ia.477     Cl       CH.sub.3 2-F-phenyl                                       Ia.478     H        CN       2-F-phenyl                                       Ia.479     F        CN       2-F-phenyl                                       Ia.480     Cl       CN       2-F-phenyl                                       Ia.481     H        H        3-F-phenyl                                       Ia.482     F        H        3-F-phenyl                                       Ia.483     CL       H        3-F-phenyl                                       Ia.484     H        Cl       3-F-phenyl                                       Ia.485     F        Cl       3-F-phenyl                                       Ia.486     Cl       Cl       3-F-phenyl                                       Ia.487     H        Br       3-F-phenyl                                       Ia.488     F        Br       3-F-phenyl                                       Ia.489     Cl       Br       3-F-phenyl                                       Ia.490     H        CH.sub.3 3-F-phenyl                                       Ia.491     F        CH.sub.3 3-F-phenyl                                       Ia.492     Cl       CH.sub.3 3-F-phenyl                                       Ia.493     H        CN       3-F-phenyl                                       Ia.494     F        CN       3-F-phenyl                                       Ia.495     Cl       CN       3-F-phenyl                                       Ia.496     H        H        4-F-phenyl                                       Ia.497     F        H        4-F-phenyl                                       Ia.498     Cl       H        4-F-phenyl                                       Ia.499     H        Cl       4-F-phenyl                                       Ia.500     F        Cl       4-F-phenyl                                       Ia.501     Cl       Cl       4-F-phenyl                                       Ia.502     H        Br       4-F-phenyl                                       Ia.503     F        Br       4-F-phenyl                                       Ia.504     Cl       Br       4-F-phenyl                                       Ia.505     H        CH.sub.3 4-F-phenyl                                       Ia.506     F        CH.sub.3 4-F-phenyl                                       Ia.507     Cl       CH.sub.3 4-F-phenyl                                       Ia.508     H        CN       4-F-phenyl                                       Ia.509     F        CN       4-F-phenyl                                       Ia.510     Cl       CN       4-F-phenyl                                       Ia.511     H        H        2-Cl-phenyl                                      Ia.512     F        H        2-Cl-phenyl                                      Ia.513     Cl       H        2-Cl-phenyl                                      Ia.514     H        Cl       2-Cl-phenyl                                      Ia.515     F        Cl       2-Cl-phenyl                                      Ia.516     Cl       Cl       2-Cl-phenyl                                      Ia.517     H        Br       2-Cl-phenyl                                      Ia.518     F        Br       2-Cl-phenyl                                      Ia.519     Cl       Br       2-Cl-phenyl                                      Ia.520     H        CH.sub.3 2-Cl-phenyl                                      Ia.521     F        CH.sub.3 2-Cl-phenyl                                      Ia.522     Cl       CH.sub.3 2-Cl-phenyl                                      Ia.523     H        CN       2-Cl-phenyl                                      Ia.524     F        CN       2-Cl-phenyl                                      Ia.525     Cl       CN       2-Cl-phenyl                                      Ia.526     H        H        3-Cl-phenyl                                      Ia.527     F        H        3-Cl-phenyl                                      Ia.528     Cl       H        3-Cl-phenyl                                      Ia.529     H        Cl       3-Cl-phenyl                                      Ia.530     F        Cl       3-Cl-phenyl                                      Ia.531     Cl       Cl       3-Cl-phenyl                                      Ia.532     H        Br       3-Cl-phenyl                                      Ia.533     F        Br       3-Cl-phenyl                                      Ia.534     Cl       Br       3-Cl-phenyl                                      Ia.535     H        CH.sub.3 3-Cl-phenyl                                      Ia.536     F        CH.sub.3 3-Cl-phenyl                                      Ia.537     Cl       CH.sub.3 3-Cl-phenyl                                      Ia.538     H        CN       3-Cl-phenyl                                      Ia.539     F        CN       3-Cl-phenyl                                      Ia.540     Cl       CN       3-Cl-phenyl                                      Ia.541     H        H        4-Cl-phenyl                                      Ia.542     F        H        4-Cl-phenyl                                      Ia.543     CL       H        4-Cl-phenyl                                      Ia.544     H        Cl       4-Cl-phenyl                                      Ia.545     F        Cl       4-Cl-phenyl                                      Ia.546     Cl       Cl       4-Cl-phenyl                                      Ia.547     H        Br       4-Cl-phenyl                                      Ia.548     F        Br       4-Cl-phenyl                                      Ia.549     Cl       Br       4-Cl-phenyl                                      Ia.550     H        CH.sub.3 4-Cl-phenyl                                      Ia.551     F        CH.sub.3 4-Cl-phenyl                                      Ia.552     Cl       CH.sub.3 4-Cl-phenyl                                      Ia.553     H        CN       4-Cl-phenyl                                      Ia.554     F        CN       4-Cl-phenyl                                      Ia.555     Cl       CN       4-Cl-phenyl                                      Ia.556     H        H        2-CH.sub.3 -phenyl                               Ia.557     F        H        2-CH.sub.3 -phenyl                               Ia.558     Cl       H        2-CH.sub.3 -phenyl                               Ia.559     H        Cl       2-CH.sub.3 -phenyl                               Ia.560     F        Cl       2-CH.sub.3 -phenyl                               Ia.561     Cl       CI       2-CH.sub.3 -phenyl                               Ia.562     H        Br       2-CH.sub.3 -phenyl                               Ia.563     F        Br       2-CH.sub.3 -phenyl                               Ia.564     Cl       Br       2-CH.sub.3 -phenyl                               Ia.565     H        CH.sub.3 2-CH.sub.3 -phenyl                               Ia.566     F        CH.sub.3 2-CH.sub.3 -phenyl                               Ia.567     Cl       CH.sub.3 2-CH.sub.3 -phenyl                               Ia.568     H        CN       2-CH.sub.3 -phenyl                               Ia.569     F        CN       2-CH.sub.3 -phenyl                               Ia.570     Cl       CN       2-CH.sub.3 -phenyl                               Ia.571     H        H        3-CH.sub.3 -phenyl                               Ia.572     F        H        3-CH.sub.3 -phenyl                               Ia.573     Cl       H        3-CH.sub.3 -phenyl                               Ia.574     H        Cl       3-CH.sub.3 -phenyl                               Ia.575     F        Cl       3-CH.sub.3 -phenyl                               Ia.576     Cl       Cl       3-CH.sub.3 -phenyl                               Ia.577     H        Br       3-CH.sub.3 -phenyl                               Ia.578     F        Br       3-CH.sub.3 -phenyl                               Ia.579     CL       Br       3-CH.sub.3 -phenyl                               Ia.580     H        CH.sub.3 3-CH.sub.3 -phenyl                               Ia.581     F        CH.sub.3 3-CH.sub.3 -phenyl                               Ia.582     Cl       CH.sub.3 3-CH.sub.3 -phenyl                               Ia.583     H        CN       3-CH.sub.3 -phenyl                               Ia.584     F        CN       3-CH.sub.3 -phenyl                               Ia.585     Cl       CN       3-CH.sub.3 -phenyl                               Ia.586     H        H        4-CH.sub.3 -phenyl                               Ia.587     F        H        4-CH.sub.3 -phenyl                               Ia.588     Cl       H        4-CH.sub.3 -phenyl                               Ia.589     H        Cl       4-CH.sub.3 -phenyl                               Ia.590     F        Cl       4-CH.sub.3 -phenyl                               Ia.591     Cl       Cl       4-CH.sub.3 -phenyl                               Ia.592     H        Br       4-CH.sub.3 -phenyl                               Ia.593     F        Br       4-CH.sub.3 -phenyl                               Ia.594     Cl       Br       4-CH.sub.3 -phenyl                               Ia.595     H        CH.sub.3 4-CH.sub.3 -phenyl                               Ia.596     F        CH.sub.3 4-CH.sub.3 -phenyl                               Ia.597     Cl       CH.sub.3 4-CH.sub.3 -phenyl                               Ia.598     H        CN       4-CH.sub.3 -phenyl                               Ia.599     F        CN       4-CH.sub.3 -phenyl                               Ia.600     Cl       CN       4-CH.sub.3 -phenyl                               Ia.601     H        H        2-CF.sub.3 -phenyl                               Ia.602     F        H        2-CF.sub.3 -phenyl                               Ia.603     Cl       H        2-CF.sub.3 -phenyl                               Ia.604     H        c1       2-CF.sub.3 -phenyl                               Ia.605     F        Cl       2-CF.sub.3 -phenyl                               Ia.606     Cl       Cl       2-CF.sub.3 -phenyl                               Ia.607     H        Br       2-CF.sub.3 -phenyl                               Ia.608     F        Br       2-CF.sub.3 -phenyl                               Ia.609     Cl       Br       2-CF.sub.3 -phenyl                               Ia.610     H        CH.sub.3 2-CF.sub.3 -phenyl                               Ia.611     F        CH.sub.3 2-CF.sub.3 -phenyl                               Ia.612     CL       CH.sub.3 2-CF.sub.3 -phenyl                               Ia.613     H        CN       2-CF.sub.3 -phenyl                               Ia.614     F        CN       2-CF.sub.3 -phenyl                               Ia.615     Cl       CN       2-CF.sub.3 -phenyl                               Ia.616     H        H        3-CF.sub.3 -phenyl                               Ia.617     F        H        3-CF.sub.3 -phenyl                               Ia.618     Cl       H        3-CF.sub.3 -phenyl                               Ia.619     H        Cl       3-CF.sub.3 -phenyl                               Ia.620     F        Cl       3-CF.sub.3 -phenyl                               Ia.621     Cl       Cl       3-CF.sub.3 -phenyl                               Ia.622     H        Br       3-CF.sub.3 -phenyl                               Ia.623     F        Br       3-CF.sub.3 -phenyl                               Ia.624     Cl       Br       3-CF.sub.3 -phenyl                               Ia.625     H        CH.sub.3 3-CF.sub.3 -phenyl                               Ia.626     F        CH.sub.3 3-CF.sub.3 -phenyl                               Ia.627     Cl       CH.sub.3 3-CF.sub.3 -phenyl                               Ia.628     H        CN       3-CF.sub.3 -phenyl                               Ia.629     F        CN       3-CF.sub.3 -phenyl                               Ia.630     Cl       CN       3-CF.sub.3 -phenyl                               Ia.631     H        H        4-CF.sub.3 -phenyl                               Ia.632     F        H        4-CF.sub.3 -phenyl                               Ia.633     Cl       H        4-CF.sub.3 -phenyl                               Ia.634     H        Cl       4-CF.sub.3 -phenyl                               Ia.635     F        Cl       4-CF.sub.3 -phenyl                               Ia.636     Cl       Cl       4-CF.sub.3 -phenyl                               Ia.637     H        Br       4-CF.sub.3 -phenyl                               Ia.638     F        Br       4-CF.sub.3 -phenyl                               Ia.639     Cl       Br       4-CF.sub.3 -phenyl                               Ia.640     H        CH.sub.3 4-CF.sub.3 -phenyl                               Ia.641     F        CH.sub.3 4-CF.sub.3 -phenyl                               Ia.642     Cl       CH.sub.3 4-CF.sub.3 -phenyl                               Ia.643     H        CN       4-CF.sub.3 -phenyl                               Ia.644     F        CN       4-CF.sub.3 -phenyl                               Ia.645     Cl       CN       4-CF.sub.3 -phenyl                               Ia.646     H        H        2-CH.sub.3 O-phenyl                              Ia.647     F        H        2-CH.sub.3 O-phenyl                              Ia.648     Cl       H        2-CH.sub.3 O-phenyl                              Ia.649     H        Cl       2-CH.sub.3 O-phenyl                              Ia.650     F        Cl       2-CH.sub.3 O-phenyl                              Ia.651     Cl       Cl       2-CH.sub.3 O-phenyl                              Ia.652     H        Br       2-CH.sub.3 O-phenyl                              Ia.653     F        Br       2-CH.sub.3 O-phenyl                              Ia.654     Cl       Br       2-CH.sub.3 O-phenyl                              Ia.655     H        CH.sub.3 2-CH.sub.3 O-phenyl                              Ia.656     F        CH.sub.3 2-CH.sub.3 O-phenyl                              Ia.657     Cl       CH.sub.3 2-CH.sub.3 O-phenyl                              Ia.658     H        CN       2-CH.sub.3 O-phenyl                              Ia.659     F        CN       2-CH.sub.3 O-phenyl                              Ia.660     Cl       CN       2-CH.sub.3 O-phenyl                              Ia.661     H        H        3-CH.sub.3 O-phenyl                              Ia.662     F        H        3-CH.sub.3 O-phenyl                              Ia.663     Cl       H        3-CH.sub.3 O-phenyl                              Ia.664     H        Cl       3-CH.sub.3 O-phenyl                              Ia.665     F        Cl       3-CH.sub.3 O-phenyl                              Ia.666     Cl       Cl       3-CH.sub.3 O-phenyl                              Ia.667     H        Br       3-CH.sub.3 O-phenyl                              Ia.668     F        Br       3-CH.sub.3 O-phenyl                              Ia.669     Cl       Br       3-CH.sub.3 O-phenyl                              Ia.670     H        CH.sub.3 3-CH.sub.3 O-phenyl                              Ia.671     F        CH.sub.3 3-CH.sub.3 O-phenyl                              Ia.672     Cl       CH.sub.3 3-CH.sub.3 O-phenyl                              Ia.673     H        CN       3-CH.sub.3 O-phenyl                              Ia.674     F        CN       3-CH.sub.3 O-phenyl                              Ia.675     Cl       CN       3-CH.sub.3 O-phenyl                              Ia.676     H        H        4-CH.sub.3 O-phenyl                              Ia.677     F        H        4-CH.sub.3 O-phenyl                              Ia.678     Cl       H        4-CH.sub.3 O-phenyl                              Ia.679     H        Cl       4-CH.sub.3 O-phenyl                              Ia.680     F        Cl       4-CH.sub.3 O-phenyl                              Ia.681     Cl       Cl       4-CH.sub.3 O-phenyl                              Ia.682     H        Br       4-CH.sub.3 O-phenyl                              Ia.683     F        Br       4-CH.sub.3 O-phenyl                              Ia.684     Cl       Br       4-CH.sub.3 O-phenyl                              Ia.685     H        CH.sub.3 4-CH.sub.3 O-phenyl                              Ia.686     F        CH.sub.3 4-CH.sub.3 O-phenyl                              Ia.687     Cl       CH.sub.3 4-CH.sub.3 O-phenyl                              Ia.688     H        CN       4-CH.sub.3 O-phenyl                              Ia.689     F        CN       4-CH.sub.3 O-phenyl                              Ia.690     Cl       CN       4-CH.sub.3 O-phenyl                              Ia.691     H        H        2-CO.sub.2 CH.sub.3 -phenyl                      Ia.692     F        H        2-CO.sub.2 CH.sub.3 -phenyl                      Ia.693     Cl       H        2-CO.sub.2 CH.sub.3 -phenyl                      Ia.694     H        Cl       2-CO.sub.2 CH.sub.3 -phenyl                      Ia.695     F        Cl       2-CO.sub.2 CH.sub.3 -phenyl                      Ia.696     Cl       Cl       2-CO.sub.2 CH.sub.3 -phenyl                      Ia.697     H        Br       2-CO.sub.2 CH.sub.3 -phenyl                      Ia.698     F        Br       2-CO.sub.2 CH.sub.3 -phenyl                      Ia.699     Cl       Br       2-CO.sub.2 CH.sub.3 -phenyl                      Ia.700     H        CH.sub.3 2-CO.sub.2 CH.sub.3 -phenyl                      Ia.701     F        CH.sub.3 2-CO.sub.2 CH.sub.3 -phenyl                      Ia.702     Cl       CH.sub.3 2-CO.sub.2 CH.sub.3 -phenyl                      Ia.703     H        CN       2-CO.sub.2 CH.sub.3 -phenyl                      Ia.704     F        CN       2-CO.sub.2 CH.sub.3 -phenyl                      Ia.705     Cl       CN       2-CO.sub.2 CH.sub.3 -phenyl                      Ia.706     H        H        3-CO.sub.2 CH.sub.3 -phenyl                      Ia.707     F        H        3-CO.sub.2 CH.sub.3 -phenyl                      Ia.708     Cl       H        3-CO.sub.2 CH.sub.3 -phenyl                      Ia.709     H        Cl       3-CO.sub.2 CH.sub.3 -phenyl                      Ia.710     F        Cl       3-CO.sub.2 CH.sub.3 -phenyl                      Ia.711     Cl       Cl       3-CO.sub.2 CH.sub.3 -phenyl                      Ia.712     H        Br       3-CO.sub.2 CH.sub.3 -phenyl                      Ia.713     F        Br       3-CO.sub.2 CH.sub.3 -phenyl                      Ia.714     Cl       Br       3-CO.sub.2 CH.sub.3 -phenyl                      Ia.715     H        CH.sub.3 3-CO.sub.2 CH.sub.3 -phenyl                      Ia.716     F        CH.sub.3 3-CO.sub.2 CH.sub.3 -phenyl                      Ia.717     Cl       CH.sub.3 3-CO.sub.2 CH.sub.3 -phenyl                      Ia.718     H        CN       3-CO.sub.2 CH.sub.3 -phenyl                      Ia.719     F        CN       3-CO.sub.2 CH.sub.3 -phenyl                      Ia.720     Cl       CN       3-CO.sub.2 CH.sub.3 -phenyl                      Ia.721     H        H        4-CO.sub.2 CH.sub.3 -phenyl                      Ia.722     F        H        4-CO.sub.2 CH.sub.3 -phenyl                      Ia.723     Cl       H        4-CO.sub.2 CH.sub.3 -phenyl                      Ia.724     H        Cl       4-CO.sub.2 CH.sub.3 -phenyl                      Ia.725     F        Cl       4-CO.sub.2 CH.sub.3 -phenyl                      Ia.726     Cl       Cl       4-CO.sub.2 CH.sub.3 -phenyl                      Ia.727     H        Br       4-CO.sub.2 CH.sub.3 -phenyl                      Ia.728     F        Br       4-CO.sub.2 CH.sub.3 -phenyl                      Ia.729     Cl       Br       4-CO.sub.2 CH.sub.3 -phenyl                      Ia.730     H        CH.sub.3 4-CO.sub.2 CH.sub.3 -phenyl                      Ia.731     F        CH.sub.3 4-CO.sub.2 CH.sub.3 -phenyl                      Ia.732     Cl       CH.sub.3 4-CO.sub.2 CH.sub.3 -phenyl                      Ia.733     H        CN       4-CO.sub.2 CH.sub.3 -phenyl                      Ia.734     F        CN       4-CO.sub.2 CH.sub.3 -phenyl                      Ia.735     Cl       CN       4-CO.sub.2 CH.sub.3 -phenyl                      Ia.736     H        H        CH.sub.2 -phenyl                                 Ia.737     F        H        CH.sub.2 -phenyl                                 Ia.738     Cl       H        CH.sub.2 -phenyl                                 Ia.739     H        Cl       CH.sub.2 -phenyl                                 Ia.740     F        Cl       CH.sub.2 -phenyl                                 Ia.741     Cl       Cl       CH.sub.2 -phenyl                                 Ia.742     H        Br       CH.sub.2 -phenyl                                 Ia.743     F        Br       CH.sub.2 -phenyl                                 Ia.744     Cl       Br       CH.sub.2 -phenyl                                 Ia.745     H        CH.sub.3 CH.sub.2 -phenyl                                 Ia.746     F        CH.sub.3 CH.sub.2 -phenyl                                 Ia.747     Cl       CH.sub.3 CH.sub.2 -phenyl                                 Ia.748     H        CN       CH.sub.2 -phenyl                                 Ia.749     F        CN       CH.sub.2 -phenyl                                 Ia.750     Cl       CN       CH.sub.2 -phenyl                                 ______________________________________                                    

Furthermore, the following substituted cinnamic acid derivatives of theformula I are particularly preferred:

the compounds Ib.001-Ib.750, which differ from the correspondingcompounds Ia.001-Ia.750 in that R⁶ is methyl: ##STR4## the compoundsIc.001-Ic.750, which differ from the corresponding compoundsIa.001-Ia.750 in that R⁶ is ethyl: ##STR5## the compounds Id.001-Id.750,which differ from the corresponding compounds Ia.001-Ia.750 in that R⁶is isopropyl: ##STR6## the compounds Ie.001-Ie.750, which differ fromthe corresponding compounds Ia.001-Ia.750 in that R⁶ is cyclopropyl:##STR7## the compounds If.001-If.750, which differ from thecorresponding compounds Ia.001-Ia.750 in that R⁵ and R⁶ are each methyl:##STR8## the compounds Ig.001-Ig.750, which differ from thecorresponding compounds Ia.001-Ia.750 in that R⁵ is ethoxy: ##STR9## thecompounds Ih.001-Ih.750, which differ from the corresponding compoundsIa.001-Ia.750 in that X is NH: ##STR10## the compounds Ii.001-Ii.750,which differ from the corresponding compounds Ia.001-Ia.750 in that X isNH and R⁶ is methyl: ##STR11## the compounds Ik.001-Ik.750, which differfrom the corresponding compounds Ia.001-Ia.750 in that X is NH and R⁶ isisopropyl: ##STR12## the compounds Il.001-Il.750, which differ from thecorresponding compounds Ia.001-Ia.750 in that X is NH and R⁶ is2-methylpropyl: ##STR13## the compounds Im.001-Im.750, which differ fromthe corresponding compounds Ia.001-Ia.750 in that X is NH and R⁶ is2-methylthioethyl: ##STR14## the compounds In.001-In.750, which differfrom the corresponding compounds Ia.001-Ia.750 in that X is NH and R⁶ isbenzyl: ##STR15## the compounds Io.001-Io.750, which differ from thecorresponding compounds Ia.001-Ia.750 in that X is N(CH₃): ##STR16## thecompounds Ip.001-Ip.750, which differ from the corresponding compoundsIa.001-Ia.750 in that X is N(R⁸) and R⁸ together with R⁶ forms apropylene chain: ##STR17##

The substituted phthalimidocinnamic acid derivatives of the formula Iare obtainable by various methods, for example by one of the followingprocesses:

Process A:

Diazotization of anilines III and reaction of the resulting diazoniumsalts with propynoic acid derivatives IV in a manner known per se (cf.N. I. Granushchak et al., Zh. Organ. Ximii. (1980) 16HO12, 2578-2581) bythe Meerwein method or modifications thereof: ##STR18##

In this method, the aniline III is first converted into a suitablediazonium salt, which is then reacted with IV in the presence of acopper salt.

The phenyldiazonium salt is advantageously prepared by reacting theaniline III in an aqueous acid solution, for example in hydrochloricacid, hydrobromic acid or sulfuric acid, with a nitrite, such as sodiumnitrite or potassium nitrite, and reacting the product with thepropynoic acid derivative IV in an inert solvent in the presence of acopper halide, such as copper(I) chloride, copper(I) bromide, copper(II)chloride or copper(II) bromide.

Examples of suitable inert solvents are water, acetonitrile, ketones,such as acetone, diethyl ketone and methyl ethyl ketone, ethers, such asdioxane and tetrahydrofuran, and alcohols, such as methanol and ethanol.

A further possibility for the preparation of the phenyldiazonium salt isto react the aniline III in an anhydrous system, for example in glacialacetic acid which contains hydrogen chloride, in dioxane, absoluteethanol, tetrahydrofuran or acetonitrile or in acetone, with a nitrite,such as tert-butyl nitrite or isopentyl nitrite. In this case, thediazotization can take place in the presence of the propynoic acidderivative IV and of the copper halide.

The reaction temperature is usually from -30° to 80° C. The componentsof the diazotization reaction are usually used in a roughlystoichiometric ratio, but an excess of one of the components may beadvantageous, for example to ensure as complete conversion as possibleof the other component.

The propynoic acid derivative IV can be used in equimolar amounts, inexcess or in less than the stoichiometric amount, based on thephenyldiazonium salt. In general, a large excess, based on thephenyldiazonium salt, of propynoic acid derivative IV has provenparticularly advantageous.

The copper halide is usually used in a stoichiometric ratio, but anexcess or less than the stoichiometric amount is also possible.

Process B

Reaction of a benzaldehyde V with an ylide VI in a manner known per se(cf. for example R. S. Mali and V. J. Yadav, Synthesis (1984) 10, 862):##STR19##

Ar is an aromatic radical which, if desired, may be substituted,preferably phenyl.

Examples of suitable solvents are aromatic hydrocarbons, such as benzeneand toluene, ethers, such as diethyl ether, tetrahydrofuran and dioxane,dipolar aprotic solvents, such as dimethyl sulfoxide anddimethylformamide, and protic solvents, such as methanol and ethanol.Mixtures of the stated solvents are also suitable.

The reaction is usually carried out at from 0° C. to the boiling pointof the particular reaction mixture.

Usually, the benzaldehyde and the ylide are used in roughlystoichiometric amounts, but it is also possible to use an excess of oneof the components.

Process C

Reaction of a benzaldehyde V with a CH-acidic compound VII in a mannerknown per se (cf. for example J. March, Advanced Organic Chemistry, page835 et seq.): ##STR20##

Depending on the particular substituents and on the reaction conditions,it may be advantageous to carry out the reaction in the presence of acatalytic or roughly equivalent amount, based on VII, of a base or inthe presence of an acid.

Examples of suitable bases are alkali metal alcoholates, such as sodiummethylate, sodium ethylate and potassium tert-butylate, aromatic andaliphatic nitrogen bases, such as pyridine, piperidine, triethylamine,ammonium acetate and β-alanine, and metal hydrides such as sodiumhydride and potassium hydride.

Acids which may be used are in particular acetic acid and propionicacid.

The reaction is carried out either in the absence of a solvent or in anexcess of base or acid or in an inert solvent or diluent. For example,alcohols, such as methanol and ethanol, and ethers, such as diethylether and methyl tert-butyl ether, are suitable solvents, depending onthe reaction conditions.

The reaction can be carried out in general at from 0° C. to the boilingpoint of the reaction mixture.

Usually, the starting compounds V and VII are used in roughly equimolaramounts, but one of the components may also be used in excess.

Process D

Reaction of an activated carboxylic acid VIII with a nucleophile IX orof an activated carboxylic acid X with an alcohol HOR⁷ in a manner knownper se (cf. for example J. March, Advanced Organic Chemistry, page 348et seq.): ##STR21##

L¹ is a conventional leaving group, for example chlorine, bromine or1-imidazolyl.

If L¹ is chlorine or bromine, the presence of a base, such astriethylamine or pyridine, may be advantageous.

Examples of suitable solvents are halohydrocarbons, such as methylenechloride and 1,2-dichloroethane, aromatic hydrocarbons andhalohydrocarbons, such as benzene, toluene and chlorobenzene, ethers,such as diethyl ether, tetrahydrofuran, methyl tert-butyl ether anddioxane, dipolar aprotic solvents, such as dimethyl sulfoxide anddimethylformamide, and mixtures of such solvents.

The reaction is carried out in general at from -20° C. to the boilingpoint of the reaction mixture.

Usually, the starting compounds are used in roughly stoichiometricamounts, unless it is preferable to use one of the components in excess.

The activated carboxylic acids VIII and X where L¹ is chlorine orbromine are in turn obtainable in a manner known per se by reacting thecorresponding carboxylic acids XI or I where R⁷ is hydrogen with ahalogenating agent, for example with thionyl chloride, thionyl bromide,sulfuryl chloride, sulfuryl bromide, an organic sulfonyl choride, suchas tosyl chloride, phosphorus trichloride, phosphorus tribromide,phosphorus pentachloride, phosphorus pentabromide or phosphoryl bromide,or with a binary halogenating system, such astetrachloromethane/triphenylphosphine ortetrabromomethane/triphenylphosphine: ##STR22##

The halogenation can be carried out without a solvent or in an inertsolvent. In general, suitable solvents are, for example,halohydrocarbons, such as methylene chloride, chloroform and1,2-dichloroethane, aromatic hydrocarbons and halohydrocarbons, such asbenzene, toluene and chlorobenzene, dipolar aprotic solvents, such asacetonitrile, and carbon disulfide and ethers, such as diethyl ether,methyl tert-butyl ether and tetrahydrofuran, depending on thehalogenating agent. Mixtures of these solvents are also suitable.

The halogenation can be carried out at from -30° C. to the boiling pointof the reaction mixture.

Depending on the halogenating agent, the acid to be halogenated isadvantageously used in a stoichiometric amount or in excess.

In a variant of the process, the activated carboxylic acid VIII or X isprepared in situ, particularly when L¹ is 1-imidazolyl or when Mitsunobuconditions are used (O. Mitsunobu, Synthesis 1981, 1).

Process E

Reaction of an acid derivative XII with an alkylating agent XIII or of acompound I where R⁷ is hydrogen with an alkylating agent L² R⁷ in amanner known per se: ##STR23##

L² is a conventional leaving group, such as halogen, preferablychlorine, bromine or iodine, alkyl- or haloalkylsulfonyloxy, preferablymethylsulfonyloxy or trifluoromethylsulfonyloxy, arylsulfonyloxy,preferably toluenesulfonyloxy, or alkoxysulfonyloxy, preferablymethoxysulfonyloxy or ethoxysulfonyloxy.

The reaction is advantageously carried out in an inert solvent, forexample in an ether, such as diethyl ether, methyl tert-butyl ether,dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran ordioxane, a ketone, such as acetone, diethyl ketone, ethyl methyl ketoneor cyclohexanone, a dipolar aprotic solvent, such as acetonitrile,dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide, a proticsolvent, such as methanol or ethanol, an aromatic hydrocarbon orhalohydrocarbon, such as benzene, chlorobenzene or 1,2-dichlorobenzene,a heteroaromatic solvent, such as pyridine or quinoline, or a mixture ofsuch solvents.

Tetrahydrofuran, acetone, diethyl ketone and dimethylformamide areparticularly suitable.

The alkylations are usually carried out in the presence of a base, forexample the hydroxides, hydrides, alkoxides, carbonates or bicarbonatesof alkali metal and alkaline earth metal cations, or tertiary aliphaticamines, such as triethylamine, N-methylmorpholine andN-ethyl-N,N-diisopropylamine, and bicyclic and tricyclic amines, such asdiazabicycloundecane (DBU) and diazabicyclooctane (DABCO), and aromaticnitrogen bases, such as pyridine, 4-dimethylaminopyridine and quinoline,being suitable. Combinations of different bases are also possible.Preferred bases are sodium hydride, sodium hydroxide, sodium carbonate,potassium carbonate, sodium methylate, sodium ethylate and potassiumtert-butylate.

Usually, the starting materials are used in roughly stoichiometricamounts, but an excess of one or other component may also beadvantageous with regard to carrying out the process or for ensuring ascomplete conversion as possible of XII or of I where R⁷ is hydrogen.

The molar ratio of acid derivative XII, or I where R⁷ is hydrogen, tobase is in general from 1:1 to 1:3.

The concentration of the starting materials in the solvent is usuallyfrom about 0.1 to 5.0 mol/l.

The reaction can be carried out at from 0° C. to the boiling point ofthe particular reaction mixture.

Process F

Reaction of a tetrahydrophthalic anhydride XIV with an aminocinnamicacid derivative IIa in a manner known per se: ##STR24##

Examples of suitable solvents/diluents are alkanecarboxylic acids, suchas acetic acid, propionic acid and isobutyric acid, alkanecarboxylicesters, such as ethyl acetate, aprotic solvents, such asdimethylformamide, dimethyl sulfoxide and N-methylpyrrolidone, andaromatics, such as toluene and the xylenes. When an aprotic solvent isused, it is preferable continuously to remove the water of reactionformed or to carry out acid catalysis (with, for example,p-toluenesulfonic acid, trifluoromethanesulfonic acid, etc.).

The reaction temperature is usually from 0° C. to the boiling point ofthe reaction mixture.

As a rule, the starting materials are used in roughly stoichiometricamounts, but one or other component may also advantageously be used inan amount of up to about 10 mol % less than or greater than thestoichiometric amount.

The aminocinnamic acid derivatives IIa are novel and in turn areobtainable, for example, by one of the methods described under processesA to E or in a manner known per se (cf. for example Houben-Weyl,Methoden der organischen Chemie, Vol. XI/1, 4th Edition 1957, page 431et seq.) by reduction of the corresponding nitrocinnamic acidderivatives IIb: ##STR25##

Particularly suitable reducing agents are

elemental metals, such as iron, tin and zinc,

hydrogen in the presence of suitable catalysts, such as palladium orplatinum on carbon or Raney nickel, or

complex hydrides, such as LiAlH₄ and NaBH₄, in the presence or absenceof catalysts.

Suitable solvents are usually carboxylic acids, such as acetic acid andpropionic acid, alcohols, such as methanol and ethanol, ethers, such asdiethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane,aromatics, such as benzene and toluene, and mixtures of said solvents,depending on the reducing agent.

The reactions can be carried out at from -100° C. to the boiling pointof the particular reaction mixture.

Usually, the starting compounds are used in roughly stoichiometricamounts; in individual cases, however, an excess of up to about 10 mol%of one or other component may also be advantageous.

The nitrocinnamic acid derivatives IIb are likewise novel and can beprepared, for example, by the methods described under processes A to E.

Unless stated otherwise, all processes described above areadvantageously carried out at atmospheric pressure or under theautogenous pressure of the particular reaction mixture.

Starting compounds stated for the individual processes are either knownor are obtainable in a manner known per se, for example also by one ofthe processes described.

The substituted phthalimidocinnamic acid derivatives of the formula Imay contain one or more centers of chirality and are then usuallyobtained as enantiomer or diastereomer mixtures. The mixtures can, ifdesired, be resolved into the substantially pure isomers by theconventional methods, for example by means of crystallization orchromatography over an optically active adsorbate. Pure optically activeisomers can also be prepared, for example, from corresponding opticallyactive starting materials.

The compounds I and their agriculturally useful salts are suitable, bothin the form of isomer mixtures and in the form of the pure isomers, asherbicides. The agents containing I are capable of very good control ofweeds and grass weeds in crops such as wheat, rice, corn, soybean andcotton, without significantly damaging the crops. This effect occurs inparticular at low application rates.

Depending on the particular application method, the compounds I orherbicides containing them may also be used in a further number of cropsfor eliminating undesirable plants. For example, the following crops aresuitable:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spp. altissima, Beta vulgaris spp. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa vat.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgate,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta,Medicago sativa, Musa spp., Nicotiana tabacum (N. rustica), Oleaeuropaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Piceaabies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyruscommunis, Ribes sylvestre, Ricinus communis, Saccharum officinarum,Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare),Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum,Vicia faba, Vitis vinifera und Zea mays.

Moreover, the compounds I can also be used in crops which are resistantto the action of herbicides as a result of breeding including geneticengineering methods.

The substituted phthalimidocinnamic acid derivatives I are also suitablefor the desiccation and/or defoliation of plants.

As desiccants, they are particularly suitable for drying out theabove-ground parts of crops, such as potato, rape, sunflower andsoybean. This permits completely mechanical harvesting of theseimportant crops.

Facilitating harvesting is also of economic interest and is permitted bythe concentrated dropping or reduction of the adhesion to the tree inthe case of citrus fruits, olives or other species and varieties ofpomes, drupes and indehiscent fruit. The same mechanism, ie. promotionof the formation of abscission tissue between fruit or leaf and shootpart of the plant is also essential for readily controllable defoliationof crops, in particular cotton.

Furthermore, the reduction of the time interval in which the individualcotton plants ripen leads to higher fiber quality after harvesting.

The compounds I and the herbicides containing them can be applied, forexample, in the form of directly sprayable aqueous solutions, powders,suspensions, including concentrated aqueous, oily or other suspensionsor dispersions, emulsions, oil dispersions, pastes, dusting agents,broadcasting agents or granules, by spraying, nebulizing, dusting,broadcasting or pouring. The application forms depend on the intendeduses; they should in any case ensure a very fine distribution of thenovel active ingredients.

Suitable inert assistants for the preparation of directly sprayablesolutions, emulsions, pastes or oil dispersions are essentially mineraloil fractions having a medium to high boiling point, such as keroseneand diesel oil, and coaltar oils and oils of vegetable and animalorigin, aliphatic, cyclic and aromatic hydrocarbons, for exampleparaffins, tetrahydronaphthalene, alkylated naphthalenes and derivativesthereof, alkylated benzenes and derivatives thereof, alcohols, such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones, such ascyclohexanone, strongly polar solvents, for example amines, such asN-methylpyrrolidone, and water.

Aqueous application forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. For the preparation of emulsions, pastes or oildispersions, the substances, as such or dissolved in an oil or solvent,can be homogenized in water by means of wetting agents, adherents,dispersants or emulsifiers. However, it is also possible to prepareconcentrates which consist of active ingredient, wetting agents,adherents, dispersants or emulsifiers and possibly solvent or oil andwhich are suitable for dilution with water.

Suitable surfactants are the alkali metal, alkaline earth metal andammonium salts of aromatic sulfonic acids, for example ligninsulfonic,phenolsulfonic, naphthalenesulfonic and dibutylnaphthalenesulfonic acid,and of fatty acids, alkylsulfonates, alkylarylsulfonates, alkylsulfates,lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfatedhexa-, hepta- and octadecanols and of fatty alcohol glycol ethers,condensates of sulfonated naphthalene and its derivatives withformaldehyde, condensates of naphthalene or of naphthalenesulfonic acidswith phenyl and formaldehyde, polyoxyethylene octylphenol ether,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycolether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers, polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,ligninsulfite waste liquors or methylcellulose.

Powders, broadcasting agents and dusting agents can be prepared bymixing or milling the active ingredients together with a solid carrier.

Granules, for example coated, impregnated and homogeneous granules, canbe prepared by binding the active ingredients to solid carriers. Solidcarriers are mineral earths, such as silicas, silica gels, silicates,talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite,kieselguhr, calcium sulfate, magnesium sulfate, magnesium oxide, milledplastics, fertilizers, such as ammonium sulfate, ammonium phosphate,ammonium nitrate or ureas, and vegetable products, such as grain flour,bark meal, wood meal and nutshell meal, cellulosic powders or othersolid carriers.

The concentrations of the active ingredients I in the ready-to-useformulations can be varied within wide ranges, for example from 0.01 to95, preferably from 0.5 to 90, % by weight. The active ingredients areused in a purity of from 90 to 100%, preferably from 95 to 100%(according to the NMR spectrum).

The following formulation examples illustrate the preparation of suchformulations:

I. 20 parts by weight of compound No. I.01 are dissolved in a mixturewhich consists of 80 parts by weight of alkylated benzene, 10 parts byweight of the adduct of from 8 to 10 mol of ethylene oxide with 1 mol ofN-monoethanololeamide, 5 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40mol of ethylene oxide with 1 mol of castor oil. By pouring the solutioninto 100 000 parts by weight of water and finely distributing ittherein, an aqueous dispersion which contains 0.02% by weight of theactive ingredient is obtained.

II. 20 parts by weight of compound No. I.02 are dissolved in a mixturewhich consists of 40 parts by weight of cyclohexanone, 30 parts byweight of isobutanol, 20 parts by weight of the adduct of 7 mol ofethylene oxide with 1 mol of isooctylphenol and 10 parts by weight ofthe adduct of 40 mol of ethylene oxide with 1 mol of castor oil. Bypouring the solution into 100 000 parts by weight of water and finelydistributing it therein, an aqueous dispersion which contains 0.02% byweight of the active ingredient is obtained.

III. 20 parts by weight of active ingredient No. I.13 are dissolved in amixture which consists of 25 parts by weight of cyclohexanone, 65 partsby weight of a mineral oil fraction boiling within the range from 210°to 280° C. and 10 parts by weight of the adduct of 40 mol of ethyleneoxide with 1 mol of castor oil. By pouring the solution into 100 000parts by weight of water and finely distributing it therein, an aqueousdispersion which contains 0.02% by weight of the active ingredient isobtained.

IV. 20 parts by weight of active ingredient No. I.14 are thoroughlymixed with 3 parts by weight of the sodium salt ofdiisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodiumsalt of a ligninsulfonic acid from a sulfite waste liquor and 60 partsby weight of silica gel powder, and the mixture is milled in a hammermill. By finely distributing the mixture in 20 000 parts by weight ofwater, a spray liquor which contains 0.1% by weight of the activeingredient is obtained.

V. 3 parts by weight of active ingredient No. I.24 are mixed with 97parts by weight of finely divided kaolin. A dusting agent which contains3% by weight of the active ingredient is obtained in this manner.

VI. 20 parts by weight of active ingredient No. I.15 are thoroughlymixed with 2 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcoholpolyglycol ether, 2 parts by weight of the sodium salt of aphenol/urea/formaldehyde condensate and 68 parts by weight of aparaffinic mineral oil. A stable oily dispersion is obtained.

The active ingredients I or the herbicides can be applied by thepreemergence or postemergence method. If the active ingredients are lesswell tolerated by certain crops, it is possible to use applicationmethods in which the herbicides are sprayed with the aid of the spraysin such a way that the leaves of the sensitive crops are as far aspossible not affected while the active ingredients reach the leaves ofundesirable plants growing underneath or the uncovered soil surface(post-directed, lay-by).

The application rates of active ingredient I are from 0.001 to 3.0,preferably from 0.01 to 2, kg/ha of active ingredient (a.i.), dependingon the aim of control, the season, the target plants and stage ofgrowth.

In order to broaden the action spectrum and to achieve synergisticeffects, the substituted phthalimidocinnamic acid deriratives I can bemixed with a large number of members of other groups of herbicidal orgrowth-regulating active ingredients and applied together with them.Examples of suitable components of the mixture are diazines,4H-3,1-benzoxazine derivatives, benzothiadiazinones,2,6-dinitroanilines, N-phenylcarbamates, thiocarbamates, halocarboxylicacids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils,benzofuran derivatives, cyclohexane-1,3-dione derivatives which carry,for example, a carboxyl or carbimino group in the 2 position,quinolinecarboxylic acid derivatives, imidazolinones, sulfonamides,sulfonylureas, aryloxy- and hetaryloxyphenoxypropionic acid and theirsalts, esters and amides and others.

It may also be useful to apply the compounds I, alone or in combinationwith other herbicides, also as a mixture together with further cropprotection agents, for example with pesticides or agents for controllingphytopathogenic fungi or bacteria. The miscibility with mineral saltsolutions which are used for eliminating nutrient and trace elementdeficiencies is also of interest. Nonphytotoxic oils and oilconcentrates may also be added.

PREPARATION EXAMPLE Example 1 N-{4-Chloro-5-2-(N-ethoxycarbonylmethyl-N-methylaminocarbonyl)-2-chloroethen-1-yl!-2-fluorophenyl}-3,4,5,6-tetrahydrophthalimide(compound No. I.17)

6 mmol of carbonyldiimidazole were added dropwise to a solution of 5mmol of N-4-chloro-5-(2-hydroxycarbonyl-2-chloroethen-1-yl)-2-fluorophenyl!-3,4,5,6-tetrahydrophthalimidein 50 ml of absolute tetrahydrofuran, after which stirring was carriedout for one hour at about 20° C. 5 mmol of ethyl sarcosine hydrochloridewere then added to the reaction mixture. 5 mmol of triethylamine in 5 mlof tetrahydrofuran were then added dropwise. Stirring was carried outfor 48 hours at about 20° C., after which the solvent was removed underreduced pressure from a water-jet pump. The residue was taken up inwater, after which the product was extracted with ethyl acetate. Thecombined organic phases were dried over sodium sulfate and thenevaporated down. The crude product was purified by chromatography oversilica gel (eluent: 1:2 petroleum ether/methyl tert-butyl ether). Yield:0.97 g (40%).

Example 2 N-{4-Chloro-3-2-(1-allyloxycarbonyleth-1-yloxycarbonyl)ethen-1-yl!phenyl}-3,4,5,6-tetrahydrophthalimide(compound No. I.11)

A solution of 6.5 mmol of 2-allyl 2-bromopropionate in 5 ml of absolutedimethylformamide was added dropwise at 50° C. to a mixture of 5.4 mmolof N-4-chloro-3-(2-hydroxycarbonylethen-1-yl)phenyl!-3,4,5,6-tetrahydrophthalimide,5.4 mmol of potassium carbonate and 50 ml of absolute dimethylformamide.Stirring was carried out for 10 hours at 50° C., after which thereaction mixture was cooled. The solvent was then removed under reducedpressure from a water-jet pump. The residue was taken up in water, afterwhich the product was extracted with methyl tert-butyl ether. Thecombined organic phases were dried over sodium sulfate and thenevaporated down. Yield: 2.3 g (96%).

Example 3 N-{4-Chloro-5-2-chloro-2-(1-methoxycarbonyl-1-cyclopropylmethoxycarbonyl)ethen-1-yl!-2-fluorophenyl}-3,4,5,6-tetrahydrophthalimide(compound No. I.16)

7.9 mmol of triphenylphosphine were added to a solution of 7.2 mmol ofN-{4-chloro-5-(2-hydroxycarbonyl-2-chloroethen-1-yl)-2-fluorophenyl}-3,4,5,6-tetrahydrophthalimideand 7.2 mmol of methyl 1-cyclopropyl-1-hydroxyacetate in 30 ml ofabsolute tetrahydrofuran. 7.9 mmol of diethyl azodicarboxylate in amixture of 10 ml of tetrahydrofuran and 10 ml of toluene were then addeddropwise. Stirring was carried out for 2 hours at about 20° C., afterwhich a further 3.95 mmol of triphenylphosphine and 3.95 mmol of ethylazodicarboxylate were added to the reaction mixture and stirring wasthen continued for 12 hours at about 20° C. Thereafter, 1 ml of waterwas added and, after stirring for a further 10 minutes, three pinches ofsodium sulfate were introduced into the reaction mixture. Finally, theundissolved material was filtered off and the filtrate was evaporateddown under reduced pressure from a water-jet pump. The crude product waspurified by means of chromatography over silica gel (eluent: 2:1petroleum ether/diethyl ether). Yield: 0.98 g (28%).

Table 8 lists very particularly preferred substitutedphthalimidocinnamic acid derivatives of the formula I, which wereprepared or can be prepared according to the examples:

                                      TABLE 8                                     __________________________________________________________________________     ##STR26##                                                                                              Mp.  °C.!                                    No.                                                                              R.sup.2                                                                         R.sup.4                                                                          X   R.sup.6                                                                              R.sup.7                                                                              .sup.1 H-NMR  δ in ppm!                       __________________________________________________________________________    I.01                                                                             H CH.sub.3                                                                         O   CH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                    Oil                                                 I.02                                                                             H CH.sub.3                                                                         O   C.sub.2 H.sub.5                                                                      CH.sub.2 CH.sub.3                                                                    Oil                                                 I.03                                                                             H Cl O   CH.sub.3                                                                             CH.sub.3                                                                             149-151                                             I.04                                                                             H Cl O   H      CH.sub.3                                                                             113-114                                             I.05                                                                             H Cl O   H      CH.sub.2 CH.sub.3                                                                    95                                                  I.06                                                                             H Cl O   H      C(CH.sub.3).sub.3                                                                    120-121                                             I.07                                                                             H Cl O   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                      1.00(t, 3H); 1.23(t, 3H);                                                     1.74(m, 4H); 1.93(m, 2H);                                                     2.33(m, 4H); 4.19(q, 2H);                                                     5.12(t, 1H); 7.50(dd, 1H);                                                    7.74(d, 1H); 7.95(d, 1H);                                                     8.18(s, 1H)                                         I.08                                                                             H H  O   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                      86                                                  I.09                                                                             H Br O   CH.sub.3                                                                             CH.sub.3                                                                             1.52(d, 3H); 1.72(brs, 4H);                                                   2.33(brs, 4H); 3.72(s, 3H);                                                   5.26(q, 1H); 7.49(dd, 1H);                                                    7.71(d, 1H); 7.86(d, 1H);                                                     8.37(s, 1H)                                         I.10                                                                             H Br O   C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                      1.02(t, 3H); 1.24(t, 3H);                                                     1.71(brs, 4H); 1.92(m, 2H);                                                   2.33(brs, 4H); 4.19(m, 2H);                                                   5.12(t, 1H); 7.50(dd, 1H);                                                    7.72(d, 1H); 7.87(d, 1H);                                                     8.38(s, 1H)                                         I.11                                                                             H H  O   CH.sub.3                                                                             CH.sub.2 CHCH.sub.2                                                                  1.54(d, 3H); 1.74(brs, 4H);                                                   2.34(brs, 4H); 4.65(d, 2H);                                                   5.22(m, 2H); 5.32(d, 1H);                                                     5.92(m, 1H); 7.23(d, 1H);                                                     7.44(dd, 1H); 7.66(d, 1H);                                                    7.94(d, 1H); 8.00(d, 1H)                            I.12                                                                             H H  O   OC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                      114                                                 I.13                                                                             F Cl O   CH.sub.3                                                                             C.sub.2 H.sub.5                                                                      1.36(t, 3H); 1.62(d, 3H);                                                     1.82(brs, 4H); 2.47(brs, 4H);                                                 4.27(q, 2H); 5.26(q, 1H);                                                     7.38(d, 1H); 7.98(d, 1H);                                                     8.17(s, 1H);                                        I.14                                                                             F Cl O   H      CH.sub.3                                                                             90-91                                               I.15                                                                             F Cl O   CH.sub.3                                                                             CH(CH.sub.3).sub.2                                                                   1.28(d, 3H); 1.30(d, 3H);                                                     1.61(d, 3H); 1.84(brs, 4H);                                                   2.46(brs, 4H);                                                                5.08(sept, 1H); 5.20(q, 1H);                                                  7.36(d, 1H); 7.98(d, 1H);                                                     8.16(s, 1H);                                        I.16                                                                             F Cl O   cyclopropyl                                                                          CH.sub.3                                                                             96-98                                               I.17                                                                             F Cl N(CH.sub.3)                                                                       H      C.sub.2 H.sub.5                                                                      1.23(t, 3H); 1.74(brs, 4H);                                                   2.47(brs, 4H);                                                                3.17, 3.34(s, 3H);                                                            4.17(q, 2H);                                                                  4.18, 4.36(brs, 2H);                                                          7.00, 7.12(s, 1H);                                                            7.34(m, 2H);                                        I.18                                                                             F Cl NH  H      C.sub.2 H.sub.5                                                                      132-133                                             I.19                                                                             F Cl NH  CH.sub.2 -phenyl                                                                     CH.sub.2 CH.sub.3                                                                    1.26(t, 3H); 1.86(brs, 4H);                                                   2.44(brs, 4H); 3.24(d, 2H);                                                   4.20(q, 2H); 4.92(q, 1H);                                                     7.16(d, 2H); 7.26(m, 5H);                                                     7.80(d, 1H); 8.16(s, 1H);                           I.20                                                                             F Cl NH  CH.sub.2 CH(CH.sub.3).sub.2                                                          CH.sub.3                                                                             0.99(d, 6H); 1.72(m, 3H);                                                     1.84(brs, 4H); 2.46(brs, 4H);                                                 3.78(s, 3H); 4.74(dt, 1H);                                                    7.18(d, 1H); 7.36(d, 1H);                                                     7.79(d, 1H); 8.16(s, 1H);                           I.21                                                                             F Cl NH  CH(CH.sub.3).sub.2                                                                   CH.sub.3                                                                             1.00(dd, 6H); 1.82(brs, 4H);                                                  2.45(brs, 4H); 2.48(m, 1H);                                                   3.80(s, 3H); 4.63(dd, 1H);                                                    7.28(d, 1H); 7.38(d, 1H);                                                     7.83(d, 1H); 8.15(s, 1H);                           I.22                                                                             F Cl NH  CH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                    1.30(brs, 3H); 1.55(brs, 3H);                                                 1.83(brs, 4H); 2.46(brs, 4H);                                                 4.24(brs, 2H); 4.65(brs, 1H);                                                 7.38(d, 1H); 7.55(d, 1H);                                                     7.82(d, 1H); 8.16(s, 1H);                           I.23                                                                             F Cl NH  CH.sub.3                                                                             CH.sub.3                                                                             1.58(d, 3H); 1.84(brs, 4H);                                                   2.43(brs, 4H); 3.82(s, 3H);                                                   4.86(q, 1H); 7.36(d, 1H);                                                     7.80(d, 1H); 8.18(s, 1H);                                                     9.36(brs, 1H)                                       I.24                                                                             H CH.sub.3                                                                         O   H      CH.sub.3                                                                             80-81                                               I.25                                                                             F Cl N(CH.sub.3)                                                                       H      CH.sub.3                                                                             1.82(brs, 4H); 2.44(brs, 4H);                                                 3.10-3.22(brs, 3H);                                                           3.75(s, 3H);                                                                  4.22(brs, 2H); 7.06(d, 1H);                                                   7.38(d, 1H); 7.80(brs, 1H)                          __________________________________________________________________________

Use examples (herbicidal activity)

The herbicidal activity of the substituted phthalimidocinnamic acidderivatives I was demonstrated by the following greenhouse experiments:

The culture vessels used were plastic flowerpots containing loamy sandwith about 3.0% of humus as substrate. The seeds of the test plants weresown separately according to species.

In the preemergence treatment, the active ingredients suspended oremulsified in water were applied directly after sowing, by means offinely distributing nozzles. The vessels were lightly sprinkle-irrigatedin order to promote germination and growth and were then covered withtransparent plastic covers until the plants had begun to grow. Thiscovering ensures uniform germination of the test plants, unless this hasbeen adversely affected by the active ingredients.

For the postemergence treatment, the test plants were first grown to aheight of growth of from 3 to 15 cm, depending on the form of growth,before being treated with the active ingredients suspended or emulsifiedin water. For this purpose, the test plants were either directly sownand grown in the same vessels or were first grown separately asseedlings and transplanted into the test vessels a few days before thetreatment. The application rate for the postemergence treatment was0.0625, 0.0313, 0.0156 or 0.0078 kg/ha of a.i.

The plants were kept at 10°-25° C. or 20°-35° C., according to species.The test period extended over 2 to 4 weeks. During this time, the plantswere tended and their reaction to the individual treatments wasevaluated.

Evaluation was based on a scale from 0 to 100. 100 means no emergence ofthe plants or complete destruction of at least the above-ground partsand 0 means no damage or normal course of growth.

The plants used in the greenhouse experiments consisted of the followingspecies:

    ______________________________________                                        Botanical name     Common name                                                ______________________________________                                        Amaranthus         carelessweed; redroot                                      retroflexus        pigweed;                                                                      common amaranth                                            Chenopodium album  lambsquarters; pigweed;                                                       fat-hen; white goosefoot                                   Chrysanthemum      crown daisy;                                               coronarium         garland chrysanthumum                                      Galium aparine     catchweed bedstraw                                         Ipomoea subspecies morningglory                                               Matricaria inodora false chamomille;                                                             scentless chamomille;                                                         false mayweed;                                             Polygonum persicaria                                                                             lady's thumb; redshank                                     Sida spinosa       prickly sida; teaweed                                      Solanum nigrum     black nightshade                                           Triticum aestivum  winter wheat                                               ______________________________________                                    

At an application rate of 0.0625 or 0.0313 kg/ha of a.i., compound No.I.24 had a very good action against Galium aparine and Solanum nigrum inwheat.

At an application rate of 0.0156 or 0.0078 kg/ha of a.i. in thepostemergence method, compound no. I.01 controlled Chenopodium album,Chrysanthemum coronarium, Ipomoea subspecies and Polygonum persicariabetter than the comparative compound A disclosed in EP-A 240659.##STR27##

At an application rate of 0.625 or 0.0313 kg/ha of a.i. in thepostemergence method, compound no. I.08 was more effective in the teston Amaranthus retroflexus, Chenopodium album, Ipomoea subspecies,Matricaria inodora and Sida spinosa than the comparative compounds B andC disclosed in EP-A 240659. ##STR28##

Use examples (desiccant/defoliant activity)

The test plants used were young, 4-leaf cotton plants (withoutcotyledons), which were grown under greenhouse conditions (relativehumidity from 50 to 70%; day/night temperature 27°/20° C.).

The foliage of the young cotton plants was treated to run-off withaqueous formulations of the active ingredients (with the addition of0.15% by weight, based on the spray liquor, of the fatty alcoholalkoxylate Plurafac LF 700). The amount of water applied was equivalentto 1000 l/ha. After 13 days, the number of dropped leaves and the degreeof defoliation in % were determined.

No dropping of leaves occurred in the case of the untreated controlplants.

We claim:
 1. A substituted phthalimidocinnamic acid derivative of theformula I ##STR29## where R¹ is hydrogen or C₁ -C₄ -alkyl;R² is hydrogenor halogen; R³ is cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy or C₁ -C₆ -haloalkoxy; R⁴ is hydrogen, cyano,nitro, halogen or C₁ -C₆ -alkyl; R⁵ is hydrogen, C₁ -C₆ -alkyl, C₂ -C₆-alkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -cyanoalkyl, C₁ -C₆-hydroxyalkyl, C₁ -C₁ -mercaptoalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl or C₁-C₆ -alkylthio-C₁ -C₆ -alkyl; R⁶ is one of the radicals stated under R⁵or cyano, nitro, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio,C₁ -C₆ -haloalkylthio, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₆-alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, hydroxycarbonyl-C₁ -C₆-alkyl, (C₁ -C₆ -alkylamino)carbonyl-C₁ -C₆ -alkyl, di(C₁ -C₆-alkyl)aminocarbonyl-C₁ -C₆ -alkyl, aminocarbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkyl)carbonyl-C₁ -C₆ -alkyl, C₁ -C₆ -alkoximino-C₁ -C₆ -alkyl,hydroximino-C₁ -C₆ -alkyl, di(C₁ -C₆ -alkoxy)-C₁ -C₆ -alkyl, di(C₁ -C₆-alkylthio)-C₁ -C₆ -alkyl, C₃ -C₆ -haloalkenyl, (C₁ -C₆-alkoxy)carbonyl, hydroxycarbonyl, (C₁ -C₆ -alkylamino)carbonyl, di(C₁-C₆ -alkyl)aminocarbonyl, aminocarbonyl(C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-haloalkyl)carbonyl, aryl, hetaryl, aryl-C₁ -C₆ -alkyl or hetaryl-C₁ -C₆-alkyl, where the aryl and hetaryl rings may, optionally, carry from oneto three radicals selected from the group consisting of cyano, nitro,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆-haloalkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -haloalkylthio, hydroxyl,mercapto and (C₁ -C₆ -alkoxy)carbonyl;or R⁵ and R⁶ together form atwo-membered to six-membered alkylene chain in which a methylene unitmay be replaced by oxygen or C₁ -C₄ -alkylimino; R⁷ is hydrogen, C₁ -C₆-alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₂ -C₆ -haloalkyl, C₁ -C₆-cyanoalkyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₁ -C₆ -alkylthio-C₂ -C₆-alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃-C₆ -cycloalkyl-C₁ -C₆ -alkyl,phenyl or benzyl, where the phenyl ringsmay each carry from one to three radicals selected from the groupconsisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio, C₁ -C₆-haloalkylthio and (C₁ -C₆ -alkoxy)carbonyl;and the agriculturallyuseful salts of I.
 2. A substituted phthalimidocinnamic acid derivativeof the formula I as claimed in claim 1, where R³ is halogen or cyano. 3.A substituted phthalimidocinnamic acid derivative of the formula I asclaimed in claim 1, where R² is hydrogen, fluorine or chlorine.
 4. Anamino- or nitrocinnamic acid derivative of the formula IIa or IIb##STR30## where R² to R⁷ and X have the meanings stated in claim
 1. 5. Aherbicide containing a herbicidal amount of at least one substitutedphthalimidocinnamic acid derivative of the formula I or anagriculturally useful salt of I, as claimed in claim 1, and at least oneinert liquid or solid carrier and, optionally, at least one surfactant.6. A plant desiccant or defoliant containing an amount, effective fordesiccation or defoliation, of at least one substitutedphthalimidocinnamic acid derivative of the formula I or anagriculturally useful salt of I, as claimed in claim 1, and at least oneinert liquid or solid carrier and, optionally, at least one surfactant.7. A process for the preparation of a herbicide, wherein a herbicidalamount of at least one substituted phthalimidocinnamic acid derivativeof the formula I or an agriculturally useful salt of I, as claimed inclaim 1, and at least one inert liquid or solid carrier and, optionally,at least one surfactant are mixed.
 8. A process for the preparation of adesiccant or defoliant, wherein an amount, effective for desiccation ordefoliation, of at least one substituted phthalimidocinnamic acidderivative of the formula I or an agriculturally useful salt of I, asclaimed in claim 1, and at least one inert liquid or solid carrier and,optionally, at least one surfactant are mixed.
 9. A method forcontrolling undesirable plant growth, wherein a herbicidal amount of atleast one substituted phthalimidocinnamic acid derivative of the formulaI or one agriculturally useful salt of I, as claimed in claim 1, isallowed to act on plants or their habitat or on seed.
 10. A method forthe desiccation or defoliation of plants, wherein an amount, effectivefor desiccation or defoliation, of at least one substitutedphthalimidocinnamic acid derivative of the formula I or oneagriculturally useful salt of I, as claimed in claim 1, is allowed toact on plants.
 11. A process for the preparation of a substitutedphthalimidocinnamic acid derivative of the formula I as claimed in claim1, where R⁴ is chlorine or bromine, wherein an aniline of the formulaIII ##STR31## and a propynoic acid derivative IV ##STR32## are subjectedto a Meerwein alkylation reaction.
 12. A process for the preparation ofa substituted phthalimidocinnamic acid derivative of the formula I asclaimed in claim 1, wherein a benzaldehyde of the formula V ##STR33## isreacted with an ylide of the formula VI ##STR34## where Ar is anaromatic radical which, if desired, may be substituted.
 13. A processfor the preparation of a substituted phthalimidocinnamic acid derivativeof the formula I as claimed in claim 1, where R⁴ is nitro or cyano,wherein a benzaldehyde of the formula V ##STR35## is reacted with aCH-acidic compound of the formula VII ##STR36##
 14. A process for thepreparation of a substituted phthalimidocinnamic acid derivative of theformula I as claimed in claim 1, wherein either an activated carboxylicacid of the formula VIII ##STR37## where L¹ is a conventional leavinggroup, is reacted with a nucleophile of the formula IX ##STR38## or anactivated carboxylic acid of the formula X ##STR39## is reacted with analkohol HOR⁷.
 15. A process for the preparation of a substitutedphthalimidocinnamic acid derivative of the formula I as claimed in claim1, wherein either an acid derivative XII ##STR40## is reacted with analkylating agent XIII ##STR41## where L² is a conventional leavinggroup, or a compound I as claimed in claim 1, where R⁷ is hydrogen, isreacted with an alkylating agent L² R⁷.
 16. A process for thepreparation of a substituted phthalimidocinnamic acid derivative of theformula I as claimed in claim 1, wherein a tetrahydrophthalic anhydrideof the formula XIV ##STR42## is reacted with an aminocinnamic acidderivative IIa ##STR43##
 17. A process for the preparation of anitrocinnamic acid derivative of the formula IIb as claimed in claim 4,wherein a correspondingly substituted aminocinnamic acid derivative IIais reduced.